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8/13/2019 Aryl , -Unsaturated Ketones as Efficient Precursor for Synthesis of Unsaturated 1,3-oxazine-2-amines under Solv

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I nternational Journ al of Scientifi c Research i n Knowledge (I JSRK), 1(12), pp. 580-596, 2013 Available online at http://www.ijsrpub.com/ijsrkISSN: 2322-4541; 2013 IJSRPUBhttp://dx.doi.org/10.12983/ijsrk-2013-p580-596

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Full Length Research Paper

Aryl , -Unsaturated Ketones as Efficient Precursor for Synthesis of Unsaturated1,3-oxazine-2-amines under Solvent-free Conditions

Ganesamoorthy Thirunarayanan

Department of Chemistry, Annamalai University, Annamalainagar-608002, India; Email: [email protected]

Received 17 October 2013; Accepted 21 November 2013

Abstract. Present study describes the efficient synthesis of some unsaturated 1,3-oxazine-2-amines including thirteen 4-(6-methoxy-2-naphthyl)-5,6-dihydro-6(substituted phenyl)- 4 H -1,3-oxazine-2-amines by KF/Al 2O3 catalysed solvent-freecyclization of enones with urea under microwave irradiation. The yields of the synthesized oxazines are more than 85%. Thecatalytic activity of this catalyst was studied by increasing the catalyst quantity from 0.05 to 0.25g in the step-wise cyclizationof chalcone and urea. The optimum quantity of the catalyst for this cyclization will be found to be 0.2 g. The effect of solventon the cyclization reaction was studied with conventional heating method and microwave irradiation technique.Comparatively, the microwave assisted solvent-free method gave more yields of the product. In this study, the effect ofsubstituents also studied. The electron donating substituted chalcones gave more yield than electron-withdrawing substitutedchalcones. This synthetic methodoly offers easy work-up procedure, non-hazardousness, shorter reaction time,environmentally benign reaction and better yield. The physical constants, analytical and spectroscopic data are supported forestablishment of their structure.

Key words: Unsaturated 1,3-oxazine-2- amines; , -Unsaturated ketones; KF/Al 2O3; Environmentally benign reaction; IR and NMR spectra

1. INTRODUCTION

The unsaturated 1,3-oxazine-2-amine and theirderivatives are an important six memberedheterocyclics possess one nitrogen, oxygen atom, onedouble bond and the amine group bonded in 2 nd

position carbon from oxygen (Banarjee et al.,2009;Yakovlev et al., 1994; Jacob et al., 1986). Theseoxazines are exists more than ten isomeric structuresdepend upon the relative position of unsaturation andthe hetero atoms (Manjula et al., 2009). Theseisomeric structural moieties are important for their

biological activities such as antimicrobial, anti-

plasmodial (Mathew et al., 2010), anti-cancer (Elarfiand Al-Difar, 2012), anti-depressants (Tiwari et al.,2011), cytotoxicity(Das et al., 2009), anti-osteoplastic(Zhou et al., 2006), anti-tumour (Wang etal., 2008), anti-oxidant(Ando et al., 2006), anti-tuberculosis (Benameur et al., 1996), anti-neoplastic(Roy et al., 2009), antagonists (Blaser et al., 2012),anti-inflammatory(Seal et al., 1997), anti-infectants(brudli et al., 2010), IKB kinase beta (Akhter et al.,2011) and PTP-1B inhibition (Gothi et al., 2011).These oxazine derivatives were applied for improvingthe super resolution microscope (Oh et al., 2010),

synthesis of eosinophils (Cho et al., 2006),identification and separation of neutrophils (Lee et al.,2013).

Many oxazine derivatives were used as dyes (Kass,1995a). Numerous solvent assisted and solvent-free

synthetic methods were available for the synthesis ofoxazine derivatives (Kass, 1995b). Currently,scientists, organic chemists are interested for solvent-free synthesis (Verma et al., 2013; Jung et al., 2006;MaMillan and Washburne, 2013; Thirunarayanan andSekar, 2013;) due to non-hazardousness, easy work-up

procedure, shorter reaction time and high yields.Hetero Diels-alder reaction (Manjula et al., 2009),ring closure reaction (Khalilzadeh et al., 2009), Betti

base induced condensation (Verma et al., 2013),Mannich type condensation-cyclization (Jacob et al.,1986) and cyclization of chalcones (Elarfi and Al-Difar, 2012) were used for the synthesis of oxazine

derivatives. Verma et al. (2013) have synthesisedsome benzoxazine/oxazine fused isoquinolines andnaphthyridines by solvent-free method. Elarfi and Al-difar (2012) have synthesised some 1, 3-oxazinederivatives by solvent-assisted method from chalconesand urea. Using eco-friendly method, more than 75%yield of dihydro- 2 H -benzo- and naphtho-1, 3-oxazinederivatives were prepared by Mathew et al. (2010).Efficient synthesis of some 1, 3-oxazine-4-thiones by

N-methylimidazole promoted solvent-free methodwas reported by Khalilzadeh et al. (2009). Sapkal etal., have studied the role of ammonium acetate for

solvent-free synthesis of 1,3-disubstituted-2,3-dihydro- 1H-naphyl oxazines (Sapkal et al., 2009;Turgut et al., 2007).

Within the above view, there is no informationavailable in the literature for the KF/Al 2O3 catalyzed


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solvent-free synthesis of unsaturated 1,3-oxazine-2-amines including 4-(6-methoxy-2-naphthyl)-5,6-dihydro- 4 H -1,3-oxazine-2-amines. Therefore theauthor have taken effort to synthesize 1,3-oxazine-2-amines including 4-(6-methoxy-2-naphthyl)-5,6-dihydro- 4 H -1,3-oxazine-2-amines and recorded theirinfrared and NMR spectra for establishing thestructure.

2. MATERIALS AND METHODS

2.1. General

All chemicals were used in this study were purchasedfrom Sigma-Aldrich and Merck Chemical companies.Mettler FP51 melting point apparatus was used for

determining the melting point of all synthesizedoxazines in open glass capillaries and is uncorrected.The AVATAR-300 Fourier transformspectrophotometer was used for recording infraredspectra (KBr, 4000-400 cm -1) of all oxazines in KBrdisc. The Bruker AV400 series type NMRspectrometer was utilized for recording NMR spectra

of all oxazine, operating at 400MHz for 1H and100MHz for 13C spectra in CDCl 3 solvent using TMS asinternal standard. Mass spectra of all synthesizedoxazines were recorded on SHIMADZU massspectrometer using chemical ionization technique.

2.2. Synthesis of 4-(aryl)-5,6-dihydro-6-(substitutedphenyl)- 4H -1,3-oxazine-2-amines

An appropriate equi-molar quantities of chalcones (2mmol), urea (2mmol) and 0.2 g of KF/Al 2O3 weretaken in a 50 mL beaker, closed with the lid. Thismixture was subjected to microwave irradiation for 2-4 minutes at 650W (Scheme 1) (Samsung, MicrowaveOven, 100-700W). After completion of the reaction,dichloromethane (20 mL) was added, followed by

simple filtration. The solution was concentrated andthe obtained solid was purified by re-crystallizationwith ethanol. The synthesized oxazines werecharacterized by their physical constants, IR, 1H and13C NMR and Mass spectral data (See Appendix-1 forIR, 1H NMR and Mass spectra of selectivecompounds).

Scheme 1: Synthesis of 4-aryl-5,6-dihydro-6-(substituted phenyl)- 4 H -1,3-oxazine-2-amines by KF/Al 2O3 catalyzed cyclizationof aryl chalcones and urea under microwave irradiation.

3. RESULTS AND DISCUSSIONS

Attempts made for synthesis of oxazine derivatives by cyclization of chalcones possess electron with-drawing as well as electron donating substituents, ureaand in the presence of catalyst KF/Al 2O3 undermicrowave irradiation. Hence the author have

synthesized some substituted 1,3-oxazine derivatives by the cyclization of 2 mmole of chalcone, 2 mmole

of urea under microwave irradiation with 0.2g ofKF/Al 2O3 catalyst at 550W for 4-6 minutes (SamsungGrill, GW73BD Microwave oven, 230V A/c, 50Hz,2450Hz, 100-750W (IEC-705), (Scheme 1). Duringthe course of this reaction KF/Al 2O3 catalyzes


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International Journal of Scientific Research in Knowledge (IJSRK), 1(12), pp. 580-596, 2013

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cyclization between chalcone and urea followed byrearrangement gave the 1, 3-oxazine-2-amines. Theyield of the oxazine in this reaction is more than 80%.The chalcone containing electron donating substituent(OCH

3) gave higher yields than electron-withdrawing

(halogens, NO 2) substituents. Further we haveinvestigated this cyclization reaction with equi-molarquantities of the styryl 6-methoxy-2-naphthyl ketone(entry 11) and urea under the same condition asabove. In this reaction the obtained yield was 90%.The effect of catalyst on this reaction was studied byvarying the catalyst quantity from 0.05 g to 0.25 g.As the catalyst quantity is increased from 0.05 to 0.25g, the percentage of yield of product is increased from84 to 90%.

Further increase in the catalyst amount beyond 0.2

g, there is no significant increase in the percentage of

the product. The effect of catalyst loading is shown inFig. 1. The optimum quantity of catalyst loading wasfound to be 0.2 g. The results, analytical and massspectral data are summarized in Table 1 (SeeAppendix-1 for IR, 1H NMR and Mass spectra ofselective compounds). The effect of solvents on theyield was also studied with methanol, ethanol,dichloromethane and tetrahydrofuran from eachcomponent of the catalyst (entry 11). Similarly theeffect of microwave irradiation was studied on eachcomponent of the catalyst. The effect of solvents onthe yield of oxazines derivatives was presented inTable 2. From the table, highest yield of oxazinesobtained from the cyclization of chalcone and ureawith the catalyst KF/Al 2O3 in microwave irradiation.The infrared and nmr spectroscopic data of selective

1,3-oxazine-2-amines are summarized in Table 3.

Fig. 1: The effect of catalyst loading


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Table 1: Analytical, physical constants, yield and mass fragment of 4-aryl-5,6-dihydro-6(substituted phenyl)- 4 H -1,3-oxazine-2-amines

Entry R R M.W. Yield(%)

m.p.(C) Mass (m/z)

1 252 83 134-136 252[M +], 236, 175, 160, 84, 77, 43, 42, 16

2 HO

268 80 144-145(145-146)[ 6]

268[M +], 252, 251, 236, 175, 160, 99, 93, 84,77,43, 42, 16

3

N

CH 3

CH 3

295 82 65-66(65-66)[ 6]

295[M +], 280, 265, 279, 251, 236, 175, 160,118, 84, 77, 44, 43, 42, 30, 16, 15

4 OCH 3

282 80 122-123 282[M +], 266, 251, 236, 205, 190, 175, 160,107, 91, 84, 77, 43, 42, 31, 16

5

Cl

288 84 115-116 286[M +], 288[M 2+], 270, 266, 251, 175, 160,111, 107, 99, 84, 77, 43, 42, 35, 16

6

H 3 CO

282 88 132-133 282[M +], 266, 251, 256, 236, 205, 190, 175,160, 107, 91, 84, 77, 43, 42, 31, 16


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7

H 3 C

266 86 112-113 266[M +], 251, 250, 175, 160, 91, 84, 77, 43,42, 31, 16, 15

8

O 2 N

297 84 141-142 297[M +], 281, 251, 175, 168, 160, 122, 84,77, 45, 43, 42, 16

9 302 87 98-99 302[M +], 286, 225, 210, 159, 127, 99, 84,77, 52, 43, 42, 16

10 302 86 109-110 302[M +], 286, 320, 301, 278,259, 225,175,161, 127, 99, 91, 84, 77, 52, 43, 42,35,16

11

H 3 CO

332 90 106-107 332[M], 317, 316, 305, 255,225, 210, 175,168, 157, 124, 99, 91, 84, 77, 59, 43, 42, 31,16,15,

12

H 3 CO

NH 2

347 85 114-115 347[M +], 331, 316, 255, 198, 190, 175, 168,157, 134, 92, 91, 77, 43, 42, 31, 16, 15,


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13

H 3 CO

NH 2

347 85 117-119 347[M +], 331, 255, 198, 175, 168, 157, 92,91, 77, 43, 42, 31, 16, 15,

14

H 3 CO

Br

411 87 128-129 411[M +], 413[M 2+], 331, 316, 255, 240, 210,157, 154, 91, 84, 77, 43, 42, 31, 16, 15

15

H 3 CO

Cl

366 88 116-117 366[M +], 368[M 2+], 335, 331, 278, 255, 209,182,168, 157, 154, 127, 111, 99, 91, 77, 58,35, 31, 16, 15

16

H 3 CO

Cl

366 89 122-123 366[M +], 368[M 2+], 335, 331, 278, 255,182,168, 157, 127, 111, 91, 77, 58, 43, 42, 35,31, 16, 15

17

H 3 CO

N

CH 3

CH 3

375 91 137-138 375[M +], 360, 359, 345, 344, 331, 255, 218,

203, 161, 157, 120, 99, 91, 77, 44, 43, 42, 31,30,16, 15,

18

H 3 CO

OH

348 86 112-113 348[M +], 332, 331, 317, 255, 191, 157, 127,99, 93, 91, 77, 58, 42, 31, 17, 16, 15,


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19

H 3 CO

OCH 3

362 91 148-149 362[M +], 347, 331, 304, 255, 205, 198, 164,157, 107, 93, 91, 77, 58, 43, 42, 31, 16,15,

20

H 3 CO

CH 3

346 90 118-119 346[M +], 331, 330, 315, 255, 189, 157, 15,99, 93, 91, 77, 58, 43, 42, 31, 16, 15,

21

H 3 CO

O 2 N

377 87 135-136 377[M +], 361, 346, 331, 319, 255, 220, 212,205, 198, 179, 165, 157, 122, 91, 84, 77, 58,46, 43, 41, 31, 16, 15

22

H 3 CO

NO 2

377 84 125-126 377[M +], 361, 346, 331, 319, 255, 220, 205,198, 165, 157, 91, 84, 77, 46, 43, 41, 31, 16,15,

23

H 3 CO

NO 2

377 85 128-129 377[M +], 361, 331, 319, 255, 220, 212, 198,

179, 165, 157, 91, 84, 77, 58, 43, 41, 31, 16,15


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Table 2: The effect of solvents in conventional heating and without solvent in microwave irradiation on yield of oxazine amine(entry 11).

Solvents MW

MeOH EtOH DCM THF

59 62 60 68 90

MeOH=Methanol; EtOH=Ethanol; DCM= Dichloromethane; THF=Tetrahydrofuran; MW=Microwave

4. CONCLUSIONS

Some unsaturated 1,3-oxazine-2-amine derivativesincluding 4-(6-methoxy-2-naphthyl)-5,6-dihydro-6-(substituted phenyl)- 4 H -1,3-oxazine-2-amines have

been synthesized by solvent free cyclization of arylchalcone and urea in presence of KF/Al 2O3 catalystunder microwave irradiation. This syntheticmethodology offers solvent-free cyclization, non-hazardous, shorter reaction time, easy-workup

procedure and better yields. The analytical andspectral data were supported for these oxazinesderivatives.

ACKNOWLEDGEMENT

The author thank to DST NMR facility, Departmentof Chemistry, Annamalai University,Annamalainagar-608 002, India for recording NMR

spectral of compounds.

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20J%5BAuthor%5D&cauthor=true&cauthor_uid=21171899http://www.ncbi.nlm.nih.gov/pubmed?term=Ali%20P%5BAuthor%5D&cauthor=true&cauthor_uid=21171899http://www.ncbi.nlm.nih.gov/pubmed?term=Meshram%20J%5BAuthor%5D&cauthor=true&cauthor_uid=21171899http://www.ncbi.nlm.nih.gov/pubmed?term=Tiwari%20V%5BAuthor%5D&cauthor=true&cauthor_uid=21171899http://www.ncbi.nlm.nih.gov/pubmed/9547671http://www.ncbi.nlm.nih.gov/pubmed?term=Jamison%20RM%5BAuthor%5D&cauthor=true&cauthor_uid=9547671http://www.ncbi.nlm.nih.gov/pubmed?term=Jamison%20RM%5BAuthor%5D&cauthor=true&cauthor_uid=9547671http://www.ncbi.nlm.nih.gov/pubmed?term=Izbicka%20E%5BAuthor%5D&cauthor=true&cauthor_uid=9547671http://www.ncbi.nlm.nih.gov/pubmed?term=Lawrence%20R%5BAuthor%5D&cauthor=true&cauthor_uid=9547671http://www.ncbi.nlm.nih.gov/pubmed?term=Von%20Hoff%20D%5BAuthor%5D&cauthor=true&cauthor_uid=9547671http://www.ncbi.nlm.nih.gov/pubmed?term=Seal%20L%5BAuthor%5D&cauthor=true&cauthor_uid=9547671http://www.ncbi.nlm.nih.gov/pubmed/19793182http://www.ncbi.nlm.nih.gov/pubmed?term=Saha%20A%5BAuthor%5D&cauthor=true&cauthor_uid=19793182http://www.ncbi.nlm.nih.gov/pubmed?term=Mitra%20I%5BAuthor%5D&cauthor=true&cauthor_uid=19793182http://www.ncbi.nlm.nih.gov/pubmed?term=Roy%20K%5BAuthor%5D&cauthor=true&cauthor_uid=19793182http://www.ncbi.nlm.nih.gov/pubmed/20615197http://www.ncbi.nlm.nih.gov/pubmed/20615197http://www.ncbi.nlm.nih.gov/pubmed?term=Lee%20BH%5BAuthor%5D&cauthor=true&cauthor_uid=20615197http://www.ncbi.nlm.nih.gov/pubmed?term=Choi%20JK%5BAuthor%5D&cauthor=true&cauthor_uid=20615197http://www.ncbi.nlm.nih.gov/pubmed?term=Lee%20S%5BAuthor%5D&cauthor=true&cauthor_uid=20615197http://www.ncbi.nlm.nih.gov/pubmed?term=Oh%20KS%5BAuthor%5D&cauthor=true&cauthor_uid=20615197http://www.archive.org/


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Table 3: Infrared and NMR spectroscopic data of 4-aryl-5,6-dihydro-6(substituted phenyl)- 4 H -1,3-oxazine-2-amines

Entry IR(, cm -1) 1H(, ppm) 13C(, ppm) NH C=N NH

( s )H4(dd )

H5(dd )

H5 (dd )

H6(dd )

Ar-H(m)

Substt. C 2 C4 C5 C6 Ar-C Substt.

1 3534 1598 2.345 2.625 2.425 2.214 4.257 6.545-7.345 --- 165.33 52.56 47.33 65.90 125.36-142.25 ---

2 3564 1628 2.295 2.598 2.465 2.201 4.351 6.289-7.258 --- 164.82 51.36 47.98 66.25 126.25-139.38 ---

3 3526 1614 2.214 2.491 2.458 2.269 4.451 6.358-7.298 3.658(s, NMe 2)

164.35 52.36 47.01 65.98 122.68-139.25 44.38 NMe 2

4 3514 1610 2.361 2.412 2.542 2.230 4.652 6.257-7.987 4.023(s, CH 3)164.03 52.28 48.74 65.39 121.36-141.25 62.38(OCH 3)

5 3536 1599 2.173 2.918 2.350 2.113 4.714 7.174-7.291 --- 164.17 52.07 47.95 67.03 126.43-139.40 ---6 3525 1621 2.277 2.753 2.299 2.217 4.593 6.781-7.352 3.997

(s,OCH 3)163.21 52.19 47.94 66.79 114.54-137.36 56.78

(OCH 3)7 3535 1597 2.187 2.811 2.246 2.176 4.669 6.956-7.378 2.536

(CH 3)164.90 52.76 47.17 66.84 125.77-139.04 25.37

(CH 3)8 3558 1624 2.317 2.897 2.436 2.223 4.709 7.273-8.165 --- 165.23 52.78 48.26 67.25 126.37-142.10 ---9 3523 1589 2.295 2.384 2.201 2.236 4.652 6.259-7.962 --- 164.99 51.36 47.29 66.25 124.37-146.02 ---10 3526 1598 2.291 2.301 2.221 2.245 4.252 6.325-7.852 --- 165.02 52.01 48.02 66.36 125.36-146.28 ---11 3553 1592 2.234 2.354 2.212 2.267 4.238 6.332-7.834 --- 165.67 52.98 47.54 66.56 121.11-139.34 ---12 3545 1592 2.114 2.243 2.224 2.329 4.667 6.554-7.933 4.867

(s, NH 2)165.46 52.72 47.26 67.36 121.76-138.65 ---

13 3532 1598 2.123 2.253 2.215 2.321 4.667 6.514-7.921 4.886(NH 2)

165.25 52.28 47.26 67.33 121.80-139.43 ---

14 3543 1606 2.223 2.222 2.276 2.043 4.646 6.723-7.734 --- 164.15 52.34 47.65 67.76 121.34-141.23 ---15 3540 1592 2.121 2.246 2.264 2.034 4.623 6.865-7.834 --- 165.35 52.42 47.63 66.65 118.75-139.76 ---16 3545 1618 2.124 2.229 2.334 2.156 4.787 6.646-7.987 3.746 164.89 52.50 47.23 66.46 118.35-139.67 ---17 3540 1602 2.034 2.248 2.378 2.138 4.769 6.638-7.978 3.723

((s, NMe 2)164.89 52.78 47.12 67.48 121.87-141.56 45.33

NMe 2 18 3553 1589 2.223 2.365 2.398 2.164 4.236 6.672-7.878 --- 165.87 52.36 47.46 66.76 118.34-139.76 ---19 3538 1634 2.242 2.246 2.338 2.126 4.334 6.848-7.968 4.247

(s,OCH 3)164.48 52.47 47.24 66.87 115.76-158.65 59.44

(OCH 3)20 3544 1623 2.219 2.236 2.259 2.136 4.483 6.296-7.869 2.39

(CH 3)164.98 52.51 47.13 66.34 114.34-148.98 24.89

(CH 3)21 3559 1622 2.334 2.232 2.334 2.121 4.667 6.822-7.534 --- 165.62 52.34 47.86 66.67 115.51-159.34 ---22 3555 1615 2.324 2.234 2.367 2.178 4.630 6.862-7.588 --- 165.40 52.33 47.86 66.78 115.74-159.98 ---23 3555 1634 2.190 2.214 2.334 2.032 4.633 6.526-7.993 --- 165.35 52.83 48.24 66.30 116.49-157.98 ---


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Appendix-1

IR spectrum of compound 11

IR spectrum of compound 14

IR spectra of compound 16


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Mass spectra of compound 11


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1H NMR spectrum of compound 11


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1H NMR Spectrum of compound 23


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Dr. G. Thirunarayanan has completed his M.Sc., degree in chemistry with first class in

Bharathidasan University, Tiruchirappalli-620 024, India. The M.Phil., and Ph.D., research degreeswere persued at Annamalai University, Annamalainagar-608 002, India in the field of PhysicalOrganic Chemistry in 1997 and 1999 respectively. His primary area of research is Synthesis, Greensynthesis, Catalysis, Spectral LFER studies, Redox LFER, biological activities of Chalcone and theirderivatives. At present Dr. G. Thirunarayanan is a Faculty Member as Assistant Professor ofChemistry at Annamalai University. He has published more than 80 research articles in reputed andrefereed national and international journals.

aryl α, β-unsaturated ketones as efficient precursor for synthesis of unsaturated...

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