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Tetrahedron Letters Vol. 54, Issue 36, 2013

Contents

COMMUNICATIONS

Synthetic studies towards tragoponol: preparation of a highly functionalized resorcylate pp 4817–4820

Hideki Miyatake-Ondozabal, Anthony G. M. Barrett*

OTBS

TBSO

O O OO

O

4 stepsMeO

OMe O

O

OMe

O O

O

OO

OTBS

OTBS

MeO

OMe O

O

OTBS

A modular synthesis of novel 4-amino-7,8-dihydro-1,6-naphthyridin-5(6H)-ones as PDE4 inhibitors pp 4821–4825

Manel Ferrer, Richard S. Roberts*, Sara Sevilla

R2

N

NH

NH

O

R3

R1

O

R2

HO

H2N

O

R1

NH3NH2

R3

O

O

O

O

CS2 6 steps

A highly sensitive fluorescent probe for imaging hydrogen sulfide in living cells pp 4826–4829

Huatang Zhang, Ping Wang, Ganchao Chen, Hon-Yeung Cheung, Hongyan Sun*

We report a new fluorescent probe installed with double azide moieties to detect H2S selectively, with 120-fold fluorescence increment on addition of H2S.

4805

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Tetrahedron Letters

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Enantio- and diastereoselective synthesis of b-substituted-d-aminoboronic esters from nitriles pp 4830–4833

P. Veeraraghavan Ramachandran*, Wataru Mitsuhashi, Debanjan Biswas, Daniel R. Nicponski

N

RR

NHBoc

Y X

BO

O1. Reduction2. Allyl/Crotylation

3. Protection4. Hydroboration5. Ox. Elimination6. Esterification

Average dr = 99 : 1Average er = 94 : 6

Unusual nor-sesquiterpene lactone from the fruits of Illicium henryi pp 4834–4836

Ji-Feng Liu*, Ya-Feng Wang, Ya-Ping Bi, Hui-Juan Li, Lu Jia, Yue-Feng Bi, Yan-Bing Zhang*

1 2

O

O

ΟΗ

ΟΗ

O

Henrylactone F (1)

OO

OO

ΟΗ

ΟΗ

Henrylactone G (2)

Synthesis of phenanthridine and its analogues via aerobic ligand-free domino Suzuki coupling–Michael additionreaction catalyzed by in situ generated palladium-nanoparticles in water

pp 4837–4840

Munmun Ghosh, Atiur Ahmed, Shubhendu Dhara, Jayanta K. Ray*

Br

NH2

Pd (OAc)2 (10 mol %) K3PO4 (2 mmol)

TBAB (0.5 mmol) water, 90 0C 60-85 %

N

O

B(OH)2

MeCOMe

A modular approach toward the synthesis of 2,4-disubstituted pyridines pp 4841–4843

Raju Singha, Shubhendu Dhara, Jayanta K. Ray*

RAr

N

Ar Ph

N

Ar CO2MeNH

MeO2C

Ar+

NH4Cl, Et3N

MeCN

NH4Cl, Et3N

MeCN

R = CO2Me R = Ph

CHO

4806 Contents / Tetrahedron Letters 54 (2013) 4805–4816

A simple, three-component synthesis of 2-aminothiazoles using trimethylsilyl isothiocyanate pp 4844–4847

Viktor Golubev, Fedor Zubkov, Mikhail Krasavin*

R1

OBr

R2

N

SN

R2

R1 R4

Si N C S

R1

OS

R2

N

HNR3

R4

R3

HNR3

R4

+

EtOH

70 oC, 2-4 h

23 examples58 - 95%

Practical synthesis of peptide C-terminal aldehyde on a solid support pp 4848–4850

Hiroyuki Konno*, Yoshihiro Sema, Manabu Ishii, Yasunao Hattori, Kazuto Nosaka, Kenichi Akaji

A short synthesis of (2S,3S)-3-hydroxypipecolic acid pp 4851–4853

Subhash P. Chavan*, Kishor R. Harale, Kailash P. Pawar

N3

HO

O

OEtNHO

HO

HO

OH

HO

HO

O

OEt

O

OEt

N3

TBSO

O

OEtO

O

A cytotoxic decahydronaphthalenylpropenal derivative and tetrahydrofuran lignans from the stems ofCameraria latifolia

pp 4854–4858

Yulin Ren, Heebyung Chai, Michael Goetz, A. Douglas Kinghorn*

HOH

H

O

1 2

O

OH OCH3

OH

H3CO

HO

OH

Contents / Tetrahedron Letters 54 (2013) 4805–4816 4807

Efficient modification of pyrene-derivative featuring third-order nonlinear optics via the click post-functionalization pp 4859–4864

Zhaokui Jin, Dong Wang*, Xiangke Wang, Pengxia Liang, Yongsheng Mi, Huai Yang*

Synthesis of a novel tetrafluoropyridine-containing amino acid and tripeptide pp 4865–4867

Alex S. Hudson, Alex Hoose, Christopher R. Coxon, Graham Sandford, Steven L. Cobb*

HN

O

NH

O

N

F

FF

F

O

OBn

OBocHNH2N

O

OH

O

N

F

FF

F

H2NO

OH

OH

Vasicine catalyzed direct C–H arylation of unactivated arenes: organocatalytic application of an abundant alkaloid pp 4868–4871

Sushila Sharma, Manoranjan Kumar, Vishal Kumar, Neeraj Kumar*

X +catalyst, KOt-Bu

110 oC, 48 hH Ar

R RAr

X = Br, I

N

N

OH

catalyst =

A catalyst-free, three-component decarboxylative coupling of amino acids with aldehydes and H-dialkylphosphitesfor the synthesis of a-aminophosphonates

pp 4872–4875

Babak Kaboudin*, Leila Karami, Jun-ya Kato, Hiroshi Aoyama, Tsutomu Yokomatsu*

+ H P(OEt)2

O toluenereflux, 1-5 h

13 examplesup to 75% yield

N CO2H

H

+R

O

H N P(OEt)2

R

O


Influence of solvent and substituents on the reaction of N-alkylthioacetamides with dimethyl acetylenedicarboxylate:synthesis of functionalized thiophenes containing an exocyclic double bond

pp 4876–4879

Konstantin L. Obydennov*, Elena L. Klimareva, Marya F. Kosterina, Pavel A. Slepukhin, Yury Yu. Morzherin

S

MeOOC

OEWG

NR

S

MeOOC

O

EWG

NR

MeO HH

EWG = CN, C(S)NHAlk

H+

N

S

RH

CN

MeOOC

O 1

2

2 1

Ultrasound promoted expeditious, catalyst-free and solvent-free approach for the synthesis of N,N0-diarylsubstitutedformamidines at room temperature

pp 4880–4884

Bashir Ahmad Dar*, Syed Naseer Ahmad, Mohammad Arif Wagay, Altaf Hussain, Nisar Ahmad, Khursheed Ahmad Bhat,Mohammad Akbar Khuroo, Meena Sharma, Baldev Singh*

FeCl3 mediated one-pot route to nitriles pp 4885–4887

Pranab Ghosh*, Raju Subba

RO

HR N

FeCl3/DMF-reflux

NH2OH.HCl

(76-98%)

Pd-catalysed heteroarylations of 3-bromochromen-4-one via C–H bond activation of heteroarenes pp 4888–4891

Fatma Belkessam, Fazia Derridj, Liqin Zhao, Abdelhamid Elias, Mohand Aidene, Saffia Djebbar, Henri Doucet*

+KOAc, DMAc

PdCl(C3H5)(dppb)2 mol%

Z

YH

Y = O, NR or SZ = C or N

O

O

Br

O

O

Y

Z

38-90% 21 examples


Microwave-assisted cyclocondensation: a rapid and solvent-free synthesis of 3-benzyl-2H-pyrido[1,2-a]pyrimidin-2-one derivatives

pp 4892–4895

S. Satyanarayana, K. Praveen Kumar, P. Lakshmi Reddy, R. Narender*, G. Narasimhulu, B. V. Subba Reddy*

+

OAc

OMe

O

N

N

N

O

neat

μωNH2

Asymmetric conjugate addition of aldehydes to vinyl sulfone using a diaminomethylenemalononitrile organocatalyst pp 4896–4899

Yohei Kanada, Hiroki Yuasa, Kosuke Nakashima, Miho Murahashi, Norihiro Tada, Akichika Itoh, Yuji Koseki, Tsuyoshi Miura*

F3C

CF3

NH

NH NH2

CNNC

SO2PhSO2Ph Ar R

CHO+ TFA

SO2PhSO2Ph

OHCAr R

CH2Cl2, rt up to 91% ee

An unusual sterol from the mushroom Stropharia rugosoannulata pp 4900–4902

Jing Wu, Tomohiro Suzuki, Jae-Hoon Choi, Nobuhiro Yasuda, Keiichi Noguchi, Hirofumi Hirai, Hirokazu Kawagishi*

An organic dye using N-dodecyl-3-(3,6-di-tert-butylcarbazol-N-yl)carbazol-6-yl as a donor moiety for efficientdye-sensitized solar cells

pp 4903–4907

Taweesak Sudyoadsuk, Janeeya Khunchalee, Sakrawee Pansay, Pongsathorn Tongkasee, Somphob Morada, Tinnagon Kaewin,Siriporn Jungsuttiwong, Vinich Promarak*

N

N

t-Bu

t-Bu

S2

SCOOH

NCC6H13 C6H13

N S

t-Bu

t-Bu

SCOOH

NC

2

D

D π

A

Dπ

A

CCTA CFTA25H12C


Amide activation by TMSCl: reduction of amides to amines by LiAlH4 under mild conditions pp 4908–4913

B. Ravinder, S. Rajeswar Reddy, A. Panasa Reddy, Rakeshwar Bandichhor*

N

O

R3R2

R1

TMSClLAH

N R3R2

R1

HH

DCM0-10 oC, 30 min

Carbohydrate derived thiosemicarbazone and semicarbazone palladium complexes: homogeneous catalyst forC–C cross coupling reactions

pp 4914–4917

Prashant Ranjan Verma, Soumik Mandal, Parna Gupta, Balaram Mukhopadhyay*

H2NN

S

C

NHN

Pd

Cl

HO

N

dPP

O

OPh3

O O

O

O

O

Selective oxidation of bulky sulfides to sulfoxides over titanosilicates having an MWW structure in the presenceof H2O2 under organic solvent-free conditions

pp 4918–4921

Yoshihiro Kon, Toshiyuki Yokoi, Masato Yoshioka, Yumiko Uesaka, Harumi Kujira, Kazuhiko Sato*, Takashi Tatsumi*

H2O2 (30%aq.)+cat. Ti-IEZ-MWW zeolite

Organic Solvent-free

S S

O

Tandem oxidative amidation of benzyl alcohols with amine hydrochloride salts catalysed by iron nitrate pp 4922–4925

Subhash Chandra Ghosh, Joyce S. Y. Ngiam, Abdul M. Seayad, Dang Thanh Tuan, Charles W. Johannes, Anqi Chen*

N

OR2

R3OH

Fe(NO3)3.9H2O (5 mol%)

TEMPO (5 mol%), air (1 atm), rt, 2 h, thenR3R2NH.HCl, CaCO3, aq. TBHP, 60 °C

R1 R1


Synthesis and antioxidant activity of new C-3 sulfenyl indoles pp 4926–4929

Claudio C. Silveira*, Samuel R. Mendes, Josemar R. Soares, Francine N. Victoria, Débora M. Martinez, Lucielli Savegnago

N

R1

R2

R3 S S S R3

O

O

O

O

DMF, CeCl3.7H2O

80 ºC, 20 min

DMA, CeCl3.7H2O

MW, 160 °C, 20 min

N

SR1 S R3

R2

O

O

N

S

NR2R2

R1 R1

Oxone,H2O/acetone

rt, 4 h N

S

NR2R2

R1 R1

O O

Solution and solid-state conformations of 1,5-pyridine and 1,5-phenanthroline-bridged p-tert-butylcalix[8]arenederivatives

pp 4930–4933

David J. Hernández, Hugo Vázquez-Lima, Patricia Guadarrama, Diego Martínez-Otero, Ivan Castillo*

OHtBu

tBu

tBu

O

OH

HO tBu

tBu

tBu

O

HO

OH OH

tBu tBu

N N

OHtBu

tBu

tBu

O

OH

HO tBu

tBu

tBu

O

HO

OH OH

tBu tBu

N

Halogen–metal exchange reactions of bromoaryl-substituted b-lactams pp 4934–4936

Maryll Geherty, James Melnyk, Keith Chomsky, David A. Hunt*

NO

X1

Y1

X2

Y2

4a: X1=Br; X2=Y1=Y2=H4b: X2=Br; X1=Y1=Y2=H4c: Y1=Br; X1=X2=Y2=H4d: Y2=Br; X1=X2=Y1=H

NO

X1

Y1

X2

Y2

5a: X1=Li; X2=Y1=Y2=H5b: X2=Li; X1=Y1=Y2=H5c: Y1=Li; X1=X2=Y2=H5d: Y2=Li; X1=X2=Y1=H

n-BuLi

THF/-78 oCE+

NO

X1

Y1

X2

Y2

6a: X1=E; X2=Y1=Y2=H6b: X2=E; X1=Y1=Y2=H6c: Y1=E; X1=X2=Y2=H6d: Y2=E X1=X2=Y1=H

A facile route to functionalized naphthalimide dyes via copper-catalyzed C–N, C–O, and C–S cross-couplingreactions in aqueous medium

pp 4937–4941

Ghasem Rezanejade Bardajee*

O O

Br

RNH2

1,4-dioxane, reflux

O NO O

Br

RNO O

X

R

CuI, KF/Al2O3

X = NR'', O, S

R'

R' X

14 examples70-95%

H2O


A new triphenylamine fluorescent dye for sensing of cyanide anion in living cell pp 4942–4944

Yi Qu, Bin Jin, Yi Liu, Yongquan Wu, Lin Yang, Junchen Wu*, Jianli Hua*

A new fluorescent triphenylamine-based sensor 1 with larger Stokes shift (�141 nm) was developed, showing red-emitting fluorescence with high selectivityto cyanide anion in pure water and in living HeLa cells.

Novel selective fluorescent probes for sensing Zn2+ ions based on a coumarin Schiff-base pp 4945–4949

Zhan-Ke Song, Biao Dong, Ge-Juan Lei, Meng-Jiao Peng, Yuan Guo*

Zn2+

Aqueous Solution N

O

O

O

COOEt

NN

R

×

Zn2+

R = H, CH3 X

N

O

O

HO

COOEt

NN

R

Novel selective fluorescent probes for Zn2+ ions based on a C@N isomerization mechanism have been designed, synthesized and used to image intracellularZn2+ ions.

Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radicalcation induced conditions

pp 4950–4952

Xiaodong Jia*, Fangfang Peng, Chang Qing, Congde Huo, Yaxin Wang, Xicun Wang*

R1

NH2

+ CHOR2 TBPA+. (10 mol%)

CH3CN, reflux NR2

R2

R1

Novel supramolecular liquid crystal: synthesis of cyclodextrin–triphenylene column liquid crystal based on clickchemistry

pp 4953–4956

Fafu Yang*, Yingmei Zhang, Hongyu Guo, Jianrong Lin

O

O 14

6OC5H11-n

O

OC5H11-nn-C5H11O

n-C5H11OOC5H11-n

N NN

CH3O

H3C O


Preparation of c-oxo esters by Staudinger reduction of b-azidocyclopropane esters pp 4957–4959

Peiming Gu*, Xiu-Ping Wu, Yan Su, Ping Xue, Xue-Qiang Li, Bo-Lin Gong, Rui Li*

The stereoselective total synthesis of (+)-8-ethylnorlobelol from anti-1,3-aminoalcohols pp 4960–4962

B. V. Subba Reddy*, B. Phaneendra Reddy, P. Sivaramakrishna Reddy, Y. Jayasudhan Reddy, J. S. Yadav

O

HN

OTs

O

OH HN

O

OH HNHO

OTs

CN

O

H+

Convergent synthesis of hexameric naphthylene macrocycles with dicarboxylic imide appendages pp 4963–4965

Jing Yang Xue, Waka Nakanishi, Daiki Tanimoto, Daisuke Hara, Yuta Nakamura, Hiroyuki Isobe*

Concise synthesis and characterization of unsymmetric 1,3-benzoxazines by tandem reactions pp 4966–4969

Muhammad Imran, Baris Kiskan*, Yusuf Yagci*

O

N N

O

R


Enantioselective synthesis of (+)-aspercyclide A pp 4970–4972

Jimmy J. P. Sejberg, Lucy D. Smith, Robin J. Leatherbarrow, Andrew J. Beavil, Alan C. Spivey*

[Ir-cat.] (3)K3PO4, iPrOH

THF60 oC, 48 h(47-61%) 4

98.0-99.6% ee

O

C5H11 OBzBzO

2

OBz

HO C5H11

O

O

O

OH O

OH

C5H11

A

B

1 (+)-aspercyclide A

2019

14

15

O

O

O

C5H11

OH

NS

O

O O

15

A novel copper-catalyzed synthesis of functionalized alkynyl imidates and alkynyl thioimidates pp 4973–4974

Issa Yavari*, Manijeh Nematpour

MeCN, r.t

R

CuI (10 mol%)Et3N, MeCN

r.t., 8 h

Cl3C CN R' XH

NH

CCl3XR'

NH

X

R

R'

X = O, S

A convenient method for the one-step synthesis of phosphonic peptides pp 4975–4977

Marcin Skorenski, Józef Oleksyszyn, Marcin Sienczyk*

NH

R1

peptide NH2

ONH

R1HN

O

P

R2

O OOpeptide

Route AR2CHO, P(OPh)3, AcOH

orRoute BR2CHO, P(OPh)3, Cu(OTf)2, CH2Cl2

Organocatalytic enantioselective conjugate addition–cyclization domino reactions of o-N-protected aminophenyla,b-unsaturated aldehydes

pp 4978–4981

Seungpyeong Heo, Shinae Kim, Sung-Gon Kim*

NHPG

CHO+X

up to >99% ee

1. Organocatalyst(20 mol %)

LiOAc (20 mol%)RO

O

OR

O

2. Et3SiH / BF3 OEt2 NX

PG

RO

O

OR

O


Nano indium oxide catalyzed tandem cyclization of amidine with nitroolefin pp 4982–4985

Shubhanjan Mitra, Avik Kumar Bagdi, Adinath Majee*, Alakananda Hajra*

R1 NH2

NH

. HCl+

H

R2

NO2R3

HN

NR1

R2

R3K2CO3 , EtOH, 70 oC

nano In2O3

Syntheses of 50-O-desmethylterphenyllin and related p-terphenyls and their inhibitory activity of TNF-a release fromRBL-2H3 cells

pp 4986–4989

Arata Yajima*, Shota Urao, Yasukiyo Yoshioka, Naoki Abe, Ryo Katsuta, Tomoo Nukada

*Corresponding authorSupplementary data available via ScienceDirect

Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts, Chemical Engineering andBiotechnology Abstracts, Current Biotechnology Abstracts, Current Contents: Life Sciences, Current Contents: Physical,Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, Medline,PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus�.Full text available on ScienceDirect�

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