DOB: 10th August, 1992 Gender: Female Marital Status: Single Religion: Hinduism Nationality: Indian Email: mondal.susmita2000@gmail.com

Phone Number: +91-8918921188, +91-9547895490

Home Address: D/O - Ashok Kumar Mondal Vill. - Raturiya; Durgapur (mcorp.); Angadpur Dist - Paschim Bardhaman West Bengal-713215 India

Current Address D/O - Ashok Kumar Mondal Vill. - Raturiya; Durgapur (mcorp.); Angadpur Dist - Paschim Bardhaman West Bengal-713215 India

DR. SUSMITA MONDAL

Academic Summary 2015-2019

Awarded Ph.D in Sciece on 6th November, 2019 under the supervision of Dr. Alakananda Hajra from Visva-Bharati University, West Bengal, India. Title of Ph.D. Thesis: “Development of Novel, Selective and Diverse C-H Functionalization Methods for Heterocycles”

2013-2015 Master of Science (M.Sc) in Chemistry (Specialization: Organic Chemistry), Visva-Bharati, Santiniketan, West Bengal, India. [8.5 (CGPA); 1st Class]

2010-2013 Bachelor of Science (B.Sc) in Chemistry Chemistry (Hons.), Mathematics, Physics Durgapur Government College, The University of Burdwan, West Bengal, India. (75.25%, 1st Class)

2010 Higher Secondary (WBCHSE), 1st Division, 82.4%

2008 Secondary (WBBSE), 1st Division, 89.6%

Research Interest Specializations: Development of novel, selective and diverse C-H functionalization

methods for heterocycles

Development of novel methodologies for the synthesis of bioactive heterocycles

Catalytic C-H bond activation for direct C-C and C-heteroatom bond formation

Creation of functional molecules to support drug discovery efforts and materials science

Designing of catalysis, ligands, and their use for challenging C-H activation reactions

Earth-abundant transition-metal catalyzed oxidative cross-coupling reactions

Visible-light organophotoredox catalyzed C-H functionalization reactions

Organometallic chemistry and catalysis

Organic transformation using high performance catalyst

Asymmetric synthesis

Skills Skilled in synthetic organic chemistry with special emphasis on medicinal chemistry and

total synthesis. Good experience in the synthesis of pharmaceutically important heterocyclic compounds

and other biologically active molecules from milligram to gram scale. Expertise in purification of compound using column chromatography, preparative TLC

and specially having good experience to purify various compounds by crystallization method.

Handling of air and moisture sensitive reagents/reactions. Good communication and management skills. Proficient in carrying-out independent and collaborative research.

Technical Exposures Analytical Technique: NMR (Bruker, 400 MHz) [1H, 13C, DEPT, NOESY, COSY, HMBC, HSQC]

FT-IR (Shimadzu), Mass (HRMS) spectrometer

Single Crystal XRD (Bruker APEX 2)

Software Skills MS-Office

Chem Bio Draw

Mercury

X-Shell

Topspin 3.0 & 3.2 (Bruker)

Honour and Award

Professor Asima Chatterjee Young Scientist Award-2018.

Qualified National Eligibility Test (NET) June 2014, Conducted by Council of Scientific

& Industrial Research and University Grants Commission (CSIR-UGC), New Delhi.

Qualified GATE (Graduate Aptitude Test in Engineering) in 2017.

Junior Research Fellowship (JRF) and Senior Research Fellowship (SRF) from

Council of Scientific & Industrial Research (CSIR), New Delhi (www.csir.res.in).

Publications

1 2020 Org. Lett., 22, 2771 Asim Kumar Ghosh, Susmita Mondal, and Alakananda Hajra*: “Dioxygen-Triggered Oxo-Sulfonylation of Hydrazones.”

2 2020 Org. Lett., 22, 1086

Payel Ghosh, Susmita Mondal, and Alakananda Hajra*: “TBHP-Mediated oxo-sulfonylation of 2H-indazoles with sulfinic acid toward indazol-3(2H)-ones.”

3 2019 Org. Lett., 21, 5606

Mukta Singsardar, Susmita Mondal, Sudip Laru, and Alakananda Hajra*: “Organophotoredox-catalyzed C(sp2)-H difluoromethylenephosphonation of imidazoheterocycles.”

4 2019 Org. Lett., 21, 4905

Sadhanendu Samanta, Susmita Mondal, Debashis Ghosh and Alakananda Hajra*: “Rhodium-catalyzed directed C-H amidation of imidazoheterocycles with dioxazolones.”

5 2019

ACS Omega.,

4, 9049

Payel Ghosh, Susmita Mondal and Alakananda Hajra*: “Mn(III)-Mediated C-H phosphorylation of indazoles with dialkyl phosphites.”

6 2019

J. Org. Chem.,

84, 4543

Mukta Singsardar, Sudip Laru, Susmita Mondal and Alakananda Hajra*: “Visible-light-induced regioselective cross-dehydrogenative-coupling of 2H-indazoles with ethers.”

7 2018

Org. Lett.,

20, 7740

Golam Kibriya, Susmita Mondal and Alakananda Hajra*: “Visible-light-mediated synthesis of unsymmetrical diaryl sulfides via oxidative coupling of arylhydrazine with thiol.”

8 2018 J. Org. Chem., 83, 13618 Payel Ghosh, Susmita Mondal and Alakananda Hajra*: “Metal-free trifluoromethylation of indazoles.”

9 2018 ACS Omega., 3, 12505

Mukta Singsardar, Susmita Mondal, Rajib Sarkar and Alakananda Hajra*: “(Diacetoxy)iodobenzene-mediated regioselective imidation of

imidazoheterocycles with N-fluorobenzenesulfonimide.”

10 2018

Org. Biomol. Chem.,

16, 1088

Sadhanendu Samanta, Susmita Mondal and Alakananda Hajra*: “A convergent synthesis of vinyloxyimidazopyridine via Cu (I)-catalyzed three-component coupling.” [Invited as a front cover picture in Org. Biomol. Chem., 2018, 16, 1041].

11 2018 J. Org. Chem., 83, 11392 Susmita Mondal and Alakananda Hajra*: “Metal-free C-5 hydroxylation of 8-aminoquinoline amide.”

12 2018 Adv. Synth. Catal., 360, 1026

Susmita Mondal, Sadhanendu Samanta and Alakananda Hajra*: “Regioselective C-7 nitration of 8-aminoquinoline amides using tert-butyl nitrite.”

13 2018 Eur. J. Org. Chem.,

2018, 1060

Susmita Mondal, Sadhanendu Samanta and Alakananda Hajra*: “Synthesis of triazolium inner salts by thiocyanation of aldehyde-derived hydrazones.”

14 2018

Org. Biomol. Chem.,

16, 2846 Susmita Mondal and Alakananda Hajra*: “Ruthenium(II)-catalyzed remote C-H addition of 8-aminoquinoline amide to activated aldehyde.”

15 2017 Org. Lett., 19, 3751 Susmita Mondal, Sadhanendu Samanta, Mukta Singsardar and Alakananda Hajra*: “Aminomethylation of imidazoheterocycles with morpholine.”

16 2017 J. Org. Chem., 82, 4504

Susmita Mondal, Sadhanendu Samanta, Sourav Jana and Alakananda Hajra*: “(Diacetoxy)iodobenzene-mediated oxidative C-H amination of imidazopyridines at ambient temperature.”

17 2017 J. Org. Chem., 82, 13722

Golam Kibriya, Sadhanendu Samanta, Sourav Jana, Susmita Mondal and Alakananda Hajra*: “Visible light organic photoredox-catalyzed C-H alkoxylation of imidazopyridine with alcohol.”

18 2016 Adv. Synth. Catal., 358, 3633 Susmita Mondal, Sadhanendu Samanta, Sougata

Santra, Avik K. Bagdi and Alakananda Hajra*: “N,N-Dimethylformamide as a methylenating reagent: Synthesis of heterodiarylmethanes via copper-

catalyzed coupling between imidazo[1,2-a]pyridines and indoles/N,N-dimeth ylaniline.”

19 2016 Org. Biomol. Chem., 14, 5073

Sadhanendu Samanta, Sourav Jana, Susmita Mondal, Kamarul Monir, Swapan K. Chandra and Alakananda Hajra*: “Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1, 2-a]pyridines.” [Highlighted in ChemInform 2016, 47, DOI: 10.1002/chin.201641180]

20 2016 Synthesis 48, 4009

Susmita Mondal, Sadhanendu Samanta, Mukta Singsardar, Subhajit Mishra, Shubhanjan Mitra and Alakananda Hajra*: “Zwitterionic-type molten salt catalyzed iodination in water: Synthesis of Iodoimidazo Heterocycles.”

21

2016

J. Org. Chem.,

81, 10088

Sadhanendu Samanta, Susmita Mondal, Sougata Santra, Golam Kibriya and Alakananda Hajra*: “FeCl3-Catalyzed Cross-Dehydrogenative Coupling between Imidazoheterocycles and Oxoaldehydes.”

22

2016

Org. Biomol. Chem.,

14, 1432

Subhajit Mishra, Pallab Mondal, Monoranjan Ghosh, Susmita Mondal and Alakananda Hajra*: “Copper-catalyzed C-H ethoxycarbonyldifluoromet- hylation of imidazoheterocycles.”

23

2015

RSC Adv.,

5, 77534

Sourav Jana, Amrita Chakraborty, Susmita Mondal and Alakananda Hajra*: “Catalyst-free selenylation of imidazoheterocycles.”

Poster Presentations 2015, 14-17th December

Poster 11th J-NOST 2015 NISER Bhubaneswar, India.

2016, 24-27th November

Oral 12th J-NOST 2015 CSIR-CDRI, Lucknow, India.

2017, 25-26th March

Poster RTCR-2017

Visva-Bharati, India

2018, 23rd September

Oral Professor Asima Chatterjee Centenary Seminar (PACCS-2018)

University of Calcutta West Bengal, India.

2018, 12-14th February

Workshop RTIS-2018

ISERC, Visva-Bharati, India

2018, 16th March

Poster FARAEM-2018

Siksha -Bhavana, Visva-Bharati, India

2018, 15-17th November

Attendance MOSM-II Ural Federal University, Russia

Summary of My Publication

1. Aminomethylation of imidazoheterocycles with morpholine

A hitherto unreported aminomethylation occurs at C-3 of imidazopyridines with morpholine in the presence of PIDA at ambient temperature in short reaction times (Scheme 1). This methodology is also applicable to indolizine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole and indole. Interestingly, the aminomethylation involving morpholine as a source of methylene group is a new phenomenon. This protocol is of much potential for the synthesis of aminomethylated derivatives under mild reaction conditions.

N

N

N

O

N

N

N

O

HO

88%

S

83%

N

N

N

O

NCN

N

N

O81%

CH3

N

N

O

75%

CN73%

N

S N

NO

89% 91%

N

N O

CH3

N

CH3

N O78%

Selected examples:

N

NR

H

N

NR

CH2

N

O

O

HN

O

HN

rt to 50 oC5 to 15 min

Imidazopyridine BenzoimidazothiazoleIndolizine Indole up to 95% yield; 34 examples

PIDA (2 equiv)

Scheme 1: Aminomethylation of imidazo[1,2-a]pyridine

“Aminomethylation of Imidazoheterocycles with Morpholine.” Susmita Mondal,

Sadhanendu Samanta, Mukta Singsardar and Alakananda Hajra* Org. Lett., 2017, 19, 3751-

3754.

2. (Diacetoxy)iodobenzene-mediated oxidative C-H amination of imidazopyridines at ambient temperature

(Diacetoxy)iodobenzene (PIDA)-mediated direct oxidative C-H amination for the synthesis of 3-amino substituted imidazopyridines has been achieved under metal-free conditions at room temperature in short reaction times (Scheme 2). This methodology is also applicable for the regioselective amination of indolizines. Experimental results suggest that the reaction likely proceeds through a radical pathway.

Scheme 2: Direct oxidative amination of imidazopyridines

“(Diacetoxy)iodobenzene-mediated Oxidative C-H Amination of Imidazopyridines at

Ambient Temperature.” Susmita Mondal, Sadhanendu Samanta, Sourav Jana and

Alakananda Hajra* J. Org. Chem., 2017, 82, 4504-4510.

3. Metal-free C-5 hydroxylation of 8-aminoquinoline amide

Diacetoxyiodobenzene-mediated remote hydroxylation of 8-aminoquinoline amide at the C-5

position has been developed. Various aryl, heteroaryl, and aliphatic carboxamides work well

to afford the hydroxylated derivatives in good yields (Scheme 3). This protocol is scalable

and exhibits high functional group tolerance. Experimental results suggest that the reaction

likely proceeds through the single-electron-transfer pathway.

Scheme 3: Hydroxylation of 8-aminoquinoline amide

“Metal-free C-5 hydroxylation of 8-aminoquinoline amide.” Susmita Mondal and

Alakananda Hajra* J. Org. Chem., 2018, 83, 11392-11398.

4. N,N-Dimethylformamide as a methylenating reagent: Synthesis of heterodiarylmethanes via copper-catalyzed coupling between imidazo[1,2-a]pyridines and indoles/N,N-dimethylaniline

A new Cu-catalyzed efficient method for the synthesis of heterodiarylmethanes through the coupling of imidazo[1,2-a]pyridines with indoles employing N,N-dimethylformamide as a methylenating reagent has been developed (Scheme 4). A library of 3-(1H-indol-3-ylmethyl)-imidazo[1,2-a]pyridine derivatives have been synthesized under aerobic reaction conditions. This protocol is also applicable for the synthesis of (4-imidazo[1,2-a]pyridin-3-ylmethyl-phenyl)-dimethyl-amines. The method is highly selective for the hetero-couplings.

Scheme 4: DMF as a methylenating reagent: synthesis of heterodiarylmethanes

“N,N-Dimethylformamide as a Methylenating Reagent: Synthesis of Heterodiarylmethanes

via Copper-Catalyzed Coupling between Imidazo[1,2-a]pyridines and Indoles/N,N-

Dimethylaniline.” Susmita Mondal, Sadhanendu Samanta, Sougata Santra, Avik K. Bagdi

and Alakananda Hajra* Adv. Synth. Catal., 2016, 358, 3633-3641.

5. Regioselective C-7 nitration of 8-aminoquinoline amides using tert-butyl nitrite

Regioselective C-7 nitration of 8-aminoquinoline amide has been achieved using tert-butyl nitrite under metal-free conditions at ambient temperature (Scheme 5). The protocol is applicable to various aryl, heteroaryl as well as aliphatic carboxamides, and exhibits high functional group compatibility. The present method provides selective mononitrated quinoline derivatives. Experimental results suggest that the reaction likely proceeds through a radical pathway.

Scheme 5: Regioselective nitration of 8-aminoquinoline amides

“Regioselective C-7 nitration of 8-aminoquinoline amides using tert-butyl nitrite.” Susmita Mondal, Sadhanendu Samanta and Alakananda Hajra* Adv. Synth. Catal., 2018, 360, 1026-1031.

6. Ruthenium(II)-catalyzed remote C-H addition of 8-aminoquinoline amide to activated aldehyde

Ruthenium(II)-catalyzed regioselective remote C-H addition of 8-aminoquinoline amides at C-5 position to ethyl glyoxalate and 2,2,2-trifluoroacetaldehyde have been developed. The transformation affords C-5 functionalized quinolines in moderate to good yields (Scheme 6). This method is applicable to various aryl, heteroaryl as well as aliphatic carboxamides.

R NH

O

R NH

O

NN

Grignard-type additionRemote C-H activation

Scalable

H CO2Et

OH OH

CO2Et+

100 °C, 8 h

[Ru(p-Cy)Cl2]2 (5 mol %)

AgSbF6 (10 mol %)NaOAc (2 equiv)

1,2-DCE

Regioselective

21 examples up to 82% yield

79%74%

NH

O

NO

MeMe

NH

O

N

Me

NH

O

N

OH

CO2Et

OH

CO2EtMe N

H

O

N

OH

CO2Et

NH

O

N

OH

CO2EtMe

OH

CO2Et

61%79%

80%

F3C

NH

O

N

OH

CF3

69%

NH

O

N

MeOH

CO2EtCl

75%

Scheme 6: Alkylation of 8-aminoquinoline amide

“Ruthenium(II)-catalyzed remote C-H addition of 8-aminoquinoline amide to activated aldehyde.” Susmita Mondal and Alakananda Hajra* Org. Biomol. Chem., 2018, 16, 2846-2850.

7. Synthesis of triazolium inner salts by thiocyanation of aldehyde-derived hydrazones

Ammonium persulphate mediated thiocyanation of aldehyde-derived hydrazone has been carried out to afford 5-thioxo-1,2,4-triazolium inner salt under metal-free conditions at ambient temperature (Scheme 7). A library of triazolium inner salts was synthesized with broad functionalities in high yields. The reaction proceeds through thiocyanation followed by isomerization to isothiocyanate and cyclization.

Scheme 7: Synthesis of triazolium inner salts

“Synthesis of triazolium inner salts by thiocyanation of aldehyde-derived hydrazones.” Susmita Mondal, Sadhanendu Samanta and Alakananda Hajra* Eur. J. Org. Chem., 2018, 2018, 1060-1066.

8. Zwitterionic-type molten salt catalyzed iodination in water: Synthesis of iodoimidazoheterocycles

An environmentally benign protocol for the iodination of imidazoheterocycles has been developed through sp2 C-H bond functionalization with molecular iodine in water at room temperature (Scheme 8). The reaction is catalyzed by imidazole-based zwitterion-type molten salt. A library of iodo imidazo[1,2-a]pyridines with broad functionalities have been synthesized. This methodology is also applicable to imidazo[2,1-b]thiazole and imidazole scaffolds.

Scheme 8: Molten salt catalyzed iodination of imidazo[1,2-a]pyridine

“Zwitterionic-Type Molten Salt Catalyzed Iodination in Water: Synthesis of

Iodoimidazoheterocycles.” Susmita Mondal, Sadhanendu Samanta, Mukta Singsardar,

Subhajit Mishra, Shubhanjan Mitra and Alakananda Hajra* Synthesis, 2016, 48, 4009-4015.

9. Rhodium-catalyzed directed C-H amidation of imidazoheterocycles with dioxazolones

A Rh(III)-catalyzed directed ortho-amidation of 2-arylimidazoheterocycles using

dioxazolone as an amidating reagent has been developed (Scheme 9). This protocol is simple,

straightforward, and economic to afford a variety of N-(2-(imidazo[1,2-a]pyridin-2-

yl)phenyl)acetamide derivatives with excellent yields. A mechanistic study reveals that a

reversible cleavage of C-H bond might be involved in the reaction.

Scheme 9: C-H Amidation reactions of imidazoheterocycles

“Rhodium-Catalyzed Directed C-H Amidation of Imidazoheterocycles with Dioxazolones.”

Sadhanendu Samanta, Susmita Mondal, Debashis Ghosh and Alakananda Hajra* Org. Lett.,

2019, 21, 4905-4909.

10. Organophotoredox-catalyzed C(sp2)-H difluoromethylenephosphonation of imidazoheterocycles

A mild and efficient method for the direct difluoromethylenephosphonation of imidazopyridine has been developed using diethyl(bromodifluoromethyl)phosphonate as a precursor of difluoromethylphosphonate group and rose bengal as photoredox catalyst (Scheme 10). Bis(pinacolato)diboron (B2Pin2) is found to be a crucial additive in the present reaction. The present methodology is also applicable to other heterocycles like imidazo[2,1-b]thiazole, benzo[d]imidazo-[2,1-b]thiazole, and indole. The reaction possibly proceeds through a single electron transfer (SET) process.

Scheme 10: Difluoromethylenephosphonation of imidazoheterocycles

“Organophotoredox-catalyzed C(sp2)-H difluoromethylenephosphonation of

imidazoheterocycles.” Mukta Singsardar, Susmita Mondal, Sudip Laru and Alakananda

Hajra* Org. Lett., 2019, 21, 5606-5610.

11. Visible-light-mediated synthesis of unsymmetrical diaryl sulfides via oxidative coupling of arylhydrazine with thiol

A metal-free visible-light-promoted oxidative coupling between thiols and arylhydrazines has been developed to afford diaryl sulfides using a catalytic amount of rose bengal as photocatalyst under aerobic conditions at room temperature (Scheme 11). The present methodology is also applicable to benzo[d]thiazole-2-thiols, benzo[d]oxazole-2-thiol, 1H-benzo[d]imidazole-2-thiols, and 1H-imidazole-2-thiol.

Scheme 11: Synthesis of unsymmetrical diaryl sulfides

“Visible-light-mediated synthesis of unsymmetrical diaryl sulfides via oxidative coupling of

arylhydrazine with thiol.” Golam Kibriya, Susmita Mondal and Alakananda Hajra* Org.

Lett., 2018, 20, 7740-7743.

12. TBHP-Mediated oxo-sulfonylation of 2H-indazoles with sulfinic acid toward indazol-3(2H)-ones

A new and efficient oxo-sulfonylation protocol has been developed for the synthesis of N-sulfonylated indazolones employing sulfinic acid as a source of sulfonyl group under metal-free conditions at ambient air. A library of structurally diverse 1-sulfonylindazol-3(2H)-one derivatives has been synthesized in good yields. A possible mechanism involving a radical process has been proposed for this transformation.

NN R2 + N

N

O

R2TBHP

rt, 8 hR2 = aryl, alkyl

R1S

O OH

S OOCH3CN, Air

R1

R3

R3

23 examples, up to 85% yield

Scheme 11: Synthesis of 1-Sulfonylindazol-3(2H)-one

“TBHP-Mediated oxo-sulfonylation of 2H-indazoles with sulfinic acid toward indazol-

3(2H)-ones.” Payel Ghosh, Susmita Mondal and Alakananda Hajra* Org. Lett., 2020, 22,

1086-1090.

13. Dioxygen-Triggered Oxo-Sulfonylation of Hydrazones

A simple and highly efficient method for the oxo-sulfonylation of aldehyde-derived hydrazones has been developed using sulfinic acid as a source of sulfonyl group and oxygen as a green oxidant under metal-free conditions at room temperature. The present C-O and N-S bond forming difunctionalization strategy affords diversely functionalized N-acylsulfonamides in good yields. Experimental results suggest a radical mechanistic pathway of the present reaction.

Scheme 11: Synthesis of N-Acylsulfonamide from Hydrazone

“Dioxygen-Triggered Oxo-Sulfonylation of Hydrazones.” Asim Kumar Ghosh, Susmita

Mondal and Alakananda Hajra* Org. Lett. 2020, 22, 2771-2775.

14. Visible-light-induced regioselective cross-dehydrogenative-coupling of 2H-indazoles with ethers

A visible-light-promoted regioselective C(sp2)-H/C(sp3)-H cross-dehydrogenative coupling between 2H-indazoles and ethers has been achieved using catalytic amount rose bengal as an organophotoredox-catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant at ambient

temperature under aerobic conditions (Scheme 12). A variety of C-3 oxyalkylated 2H-indazoles have been synthesized in excellent to moderate yields.

Scheme 12: Cross-dehydrogenative-coupling of 2H-indazoles with ethers

“Visible-light-induced regioselective cross-dehydrogenative-coupling of 2H-indazoles with

ethers.” Mukta Singsardar, Sudip Laru, Susmita Mondal and Alakananda Hajra* J. Org.

Chem., 2019, 84, 4543-4550.

15. Metal-free trifluoromethylation of indazoles

A simple and efficient tert-butyl hydroperoxidemediated direct trifluoromethylation of indazoles using sodium trifluoromethanesulfinate has been developed under metal-free conditions (Scheme 13). A library of trifluoromethylated products with broad functionalities has been synthesized with moderate to good yields. A radical mechanistic pathway has been proposed for the present protocol.

Scheme 13: Trifluoromethylation of indazoles

“Metal-free trifluoromethylation of indazoles.” Payel Ghosh, Susmita Mondal and

Alakananda Hajra* J. Org. Chem., 2018, 83, 13618-13623.

16. Visible-light organic photoredox-catalyzed C-H alkoxylation of imidazopyridine with alcohol

Visible light mediated C-3 alkoxylation of imidazopyridines with alcohols have been achieved using rose bengal as an organic photoredox catalyst at room temperature (Scheme 14). Widely abundant air acts as the terminal oxidant that avoids the use of stoichiometric amount of peroxo-compounds. A wide range of functional groups could be tolerated under the reaction condition to produce C(sp2)-H alkoxylated products in high yields.

Scheme 14: Visible-light mediated C-3 alkoxylation of imidazopyridine

“Visible Light Organic Photoredox-Catalyzed C–H Alkoxylation of Imidazopyridine with

Alcohol.” Golam Kibriya, Sadhanendu Samanta, Sourav Jana, Susmita Mondal and

Alakananda Hajra* J. Org. Chem., 2017, 82, 13722−13727.

17. FeCl3-catalyzed cross-dehydrogenative coupling between imidazoheterocycles and oxoaldehydes

An Fe(III)-catalyzed efficient dicarbonylation of imidazoheterocycles has been developed through cross-dehydrogenative coupling between imidazoheterocycles and oxoaldehydes under ambient air in high yields (Scheme 15). The present protocol is also applicable to indolizines. Imidazopyridine produced bisimidazopyridine with arylaldehyde. Experimental results suggest that the reactions proceed through the non-radical pathway.

Scheme 15: Synthesis of vinyl ether substituted imidazo[1,2-a]pyridine

“FeCl3-Catalyzed cross-dehydrogenative coupling between imidazoheterocycles and

oxoaldehydes.” Sadhanendu Samanta, Susmita Mondal, Sougata Santra, Golam Kibriya and

Alakananda Hajra* J. Org. Chem., 2016, 81, 10088-10093.

18. Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines

A unique copper-catalyzed binucleophilic switching of 2-aminopyridine has been developed for the regioselective synthesis of 2- and 3-iodoimidazo[1,2-a]pyridines using alkene/alkyne as coupling partners in the presence of molecular iodine under aerobic reaction conditions (Scheme 16). This method was also applied to the synthesis of 2-iodo-3-phenylbenzo[d]imidazo[2,1-b]thiazoles. This protocol offers an easy access towards the synthesis of 2,3-diarylimidazo[1,2-a]pyridines.

Scheme 16: Regioselective synthesis of iodoimidazo[1,2-a]pyridines

“Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-

a]pyridines.” Sadhanendu Samanta, Sourav Jana, Susmita Mondal, Kamarul Monir, Swapan

K. Chandra and Alakananda Hajra* Org. Biomol. Chem., 2016, 14, 5073-5078.

19. Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles A regioselective copper-catalyzed ethoxycarbonyl-difluoromethylation of imidazo[1,2-a]pyridines has been developed through sp2 C-H bond functionalization with BrCF2CO2Et under ambient air (Scheme 17). A series of ethoxycarbonyldifluoromethylated imidazo[1,2-a]pyridines with broad functionalities have been synthesized. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

N N

EtO2CF2C

F

N N

EtO2CF2CN

N N

EtO2CF2C

CN

N N

EtO2CF2C

83% 58% 42% 70%

N

SN

EtO2CF2C

82%

Selected examples:

Scheme 17: Ethoxycarbonyldifluoromethylation of imidazoheterocycles

“Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles.”

Subhajit Mishra, Pallab Mondal, Monoranjan Ghosh, Susmita Mondal and Alakananda

Hajra* Org. Biomol. Chem., 2016, 14, 1432-1436.

20. A Convergent synthesis of vinyloxyimidazopyridine via Cu(I)-catalyzed three-component coupling

Synthesis of vinyloxyimidazopyridine with complete regio and stereoselectivity has been achieved by the Cu(I)-catalyzed three-component coupling of 2-aminopyridine, 2-oxoaldehyde and alkyne (Scheme 18). This protocol is operationally very simple and of much potential for the synthesis of heteroarylated vinyl ethers from basic chemicals. Steroidal imidazopyridinyl vinyl ether was obtained successfully from ethynylestradiol.

Scheme 18: Synthesis of vinyl ether substituted imidazo[1,2-a]pyridine

“A Convergent Synthesis of Vinyloxyimidazopyridine via Cu(I)-Catalyzed Three-

Component Coupling.” Sadhanendu Samanta, Susmita Mondal and Alakananda Hajra* Org.

Biomol. Chem., 2018, 16, 1088-1092.

21. (Diacetoxy)iodobenzene-mediated regioselective imidation of imidazoheterocycles with N-fluorobenzenesulfonimide

Metal-free (diacetoxy)iodobenzene-mediated regioselective imidation of imidazoheterocycles using commercially available N-fluorobenzenesulfonimide as an imidating reagent has been developed (Scheme 19). The present protocol also represents an efficient way to access the imidated derivatives of imidazo[2,1-b]thiazole, benzo[d]imidazo-[2,1-b]thiazole, indoles, and indolizines. A radical mechanistic pathway has been proposed for the present protocol.

Scheme 19: Imidation of imidazoheterocycles with N-fluorobenzenesulfonimide

“(Diacetoxy)iodobenzene-mediated regioselective imidation of imidazoheterocycles with N-

fluorobenzenesulfonimide.” Mukta Singsardar, Susmita Mondal, Rajib Sarkar and

Alakananda Hajra* ACS Omega, 2018, 3, 12505-12512.

22. Mn(III)-Mediated C-H phosphorylation of indazoles with dialkyl phosphites

A direct and efficient Mn(III) acetate-mediated phosphorylation of 2H-indazoles with dialkyl phosphites has been developed under mild reaction conditions (Scheme 20). A library of phosphorylated products with broad functionalities has been synthesized in moderate to good yields. Experimental results suggest a radical mechanistic pathway of the present protocol.

Scheme 20: C-H Phosphorylation of indazoles

“Mn(III)-Mediated C-H phosphorylation of indazoles with dialkyl phosphites.” Payel Ghosh,

Susmita Mondal and Alakananda Hajra* ACS Omega, 2019, 4, 9049-9055.

23. Catalyst-free selenylation of imidazoheterocycles

A simple, efficient, and practical method for the phenylselenylation of imidazo[1,2-a]pyridines via electrophilic substitution employing readily available phenylselenium bromide has been developed in aqueous media at room temperature (Scheme 21). A library of 3-phenylselenylimidazo[1,2-a]pyridines have been synthesized employing this methodology with high yields. The present protocol is also applicable for the phenylselenylation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

NN

SeNC

93%

NN

Se

SO

O

78%

NN

Se

CH3H3C

73%

NN

Se

78%

CH3N

N

Se

SCH3

84%

Selected examples:

Scheme 21: Selenylation of imidazoheterocycles

“Catalyst-free selenylation of imidazoheterocycles.” Sourav Jana, Amrita Chakraborty,

Susmita Mondal and Alakananda Hajra* RSC Adv., 2015, 5, 77534-77537.

DECLARATION

I, hereby declare that the above-furnished particulars are true to the best of my

knowledge and belief. If an opportunity is given, I will prove my efficiency, my loyalty

and desire to work.

Place: - Durgapur Date :- 22/05/2020 Signature