Tetrahedron Letters Vol. 54, Issue 37, 2013

Contents

COMMUNICATIONS

Synthesis of 2-substituted pyrrolidines from nitriles pp 5001–5003

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

i) Reductionii) Allylation

ROH

NH2 i) ChlorinationHNR

RCNii) Cyclizationiii) Hydroboration

iv) Oxidation 6 Steps, 18% Yield8 Examples

Used withoutPurification

≈

Easy eco-friendly phenonium ion production from phenethyl alcohols in dimethyl carbonate pp 5004–5006

M. Barontini, I. Proietti Silvestri*, V. Nardi, P. Bovicelli, L. Pari, F. Gallucci, R. Spezia, G. Righi

phenonium ion

O

R R R

S

O

O

CO2, CH3OHS

Amberlyst 15 Up to 95% yield,up to 5 catalytic cycles

S=MeOH, EtOH, TFA, anisole

Selective and sensitive turn on detection of Hg2+ in aqueous solution using a thioether-appended dipeptide pp 5007–5010

Lok Nath Neupane, Keun-Hyeung Lee*

4991

Contents lists available at ScienceDirect

Tetrahedron Letters

journal homepage: www.elsevier .com/ locate/ tet le t

An efficient reverse Diels–Alder approach for the synthesis of N-alkyl bismaleimides pp 5011–5013

Venkataramanarao Rao, Suryakiran Navath, Mohankumar Kottur, James R. McElhanon, Dominic V. McGrath*

L-Tartaric acid6 steps

O

N

OOOH

OHN

O

N

OO

Preparation of enantioenriched tetraols and triolamines from a common epoxide pp 5014–5017

Makan Kaviani-Joupari, Michael P. Schramm*

Facile synthesis of thiochromeno[2,3-b]indol-11(6H)-ones and pyrido[30,20:5,6]thiopyrano[2,3-b]indol-5(10H)-ones pp 5018–5021

Mostafa Kiamehr, Firouz Matloubi Moghaddam*, Volodymyr Semeniuchenko, Alexander Villinger, Peter Langer*,Viktor O. Iaroshenko*

X

Cl

O

+

R1 = H, Me, Et, Ph, 7-(CH2)3 R2, R3, R4 = H, FX= CH2, N; Y= Cl, F

Y

R2

R3

R4NR1

S

NR1

S

O

X R4

R3R2K2CO3,

DMF (abs)

Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes pp 5022–5025

Wioleta Borzezcka, Iván Lavandera*, Vicente Gotor*

One-pot two-step

FOH

Cl

HN NNO2

N FN

O2N

ON FN

O2N

OH

*

Enan�opureF-MISO

ADHADH

MW

4992 Contents / Tetrahedron Letters 54 (2013) 4991–5000

Highly efficient dynamic kinetic resolution of secondary aromatic alcohols using a low-cost solid super acidas a racemization catalyst

pp 5026–5030

Gang Xu, Liang Wang, Yongjun Chen, Yongmei Cheng, Jianping Wu*, Lirong Yang

Rational design, green synthesis of reaction-based dual-channel chemosensors for cyanide anion pp 5031–5034

Qi Lin, Yong-Peng Fu, Pei Chen, Tai-Bao Wei, You-Ming Zhang*

Arvestolides A–C, new rare sesquiterpenes from the aerial parts of Artemisia vestita pp 5035–5038

Shuaihua Tian, Xingyun Chai, Ke Zan, Kewu Zeng, Xiaoyu Guo, Yong Jiang*, Pengfei Tu*

O O

OHO

AcO

Highly selective recognition of fluoride anion through direct deprotonation of intramolecularly hydrogen-bondedphenolic hydroxyl groups

pp 5039–5042

Xiang Zhang, Jie Fu, Tian-Guang Zhan, Liyan Dai*, Yingqi Chen, Xin Zhao*

N

NN

N

NN

HOO

HOO

OH

OH

F-

N

NN

N

NN

OO

OO

O

O

H

H

Contents / Tetrahedron Letters 54 (2013) 4991–5000 4993

A novel one-pot synthesis of 7-methoxy-2-arylthieno[3,2-b]pyridine-3-ols in domino fashion pp 5043–5047

Srinu Puvvala, Vinod D. Jadhav*, Sheikh M. Farooq, Balaram Patro, Ch. Venkata Ramana Reddy

N

O

O

O

Ar SS Ar

N

O

SAr

OHN

O

N

O1 1A 1C

2

3

N

O

O

N

S ArLDA LDA LDA

THF-78 °C, 2h

A simple and efficient synthesis of 7-methoxy-2-arylthieno[3,2-b]pyridine-3-ols was achieved using a novel one-pot LDA-promoted domino reaction.Although this class of compounds are not very well represented in the literature, similar skeletons are of immense biological importance. A few closely relatedcompounds are reported with multi-step syntheses using harsh conditions and longer reaction time.

Catalyst-free synthesis of 3-hydroxy-3-(alkyl/aryl)indolin-2-ones by addition of organoaluminum reagents to isatins pp 5048–5051

G. Santosh Kumar, Palakuri Ramesh, A. Sanjeeva Kumar, A. Swetha, H. M. Meshram*

NO

O

R

R1

R2

R3

+

1 2

R = H, CH3, BnR1 = H, Cl, BrR2 = H, Cl, Br, I, F, OCF3, NO2R3 = H, Cl, Br

R4 = Me, Et, Ph

3

Toluene

700 CAl(R4)3

No additional catalyst

N

R1

R2

R3

HO R4

O

R

New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II pp 5052–5055

Susumu Ohira*, Kyouhei Takaya, Taichi Mitsui, Masahiro Kido, Kazuyuki Kakumoto, Ken-ichiro Hayashi, Atsuhito Kuboki,Hiroyuki Tani, Shogo Ikeda, Munekazu Iinuma, Yukihiro Akao, Hiroshi Nozaki*

One-pot esterification-click (CuAAC) and esterification–acetylene coupling (Glaser/Eglinton) for functionalizationof Wang polystyrene resin

pp 5056–5060

Sagi Eppel*, Moshe Portnoy*

4994 Contents / Tetrahedron Letters 54 (2013) 4991–5000

Tandem synthesis of highly functionalized N-phosphorylated sulfonamido-pyrazolone derivatives pp 5061–5063

Issa Yavari*, Manijeh Nematpour

NN

CO2PriCO2

iPr

NN

O

P(O)(OR")2

CO2iPr

HN

R

SO2R'

R

CuI (10 mol%)Et3N, DMFr.t., 5 h, N2

R'S

N3

O O

CRN

SO2R'

P(OR'')3 +DMF, r.t.

Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)

pp 5064–5068

Kiumars Bahrami*, Mohammad M. Khodaei*, Homa Targhan, Mehdi Sheikh Arabi

R COOHR' OH

R' NH2

H COOH RHN R"

(TAPC)P NCl

Cl

3

TAPC

grinding, r.t.

solvent-free, 50 °C

R COOR'

R CONR'

R"RN CHO+

+ 14 examples

16 examples

12 examples

Catalyst-free coupling of indole derivatives with 3,4-dihydroisoquinoline and related compounds pp 5069–5071

István Szatmári, Judit Sas, Ferenc Fülöp*

NH

NH

NH

NH

NH

RR

R

S

R = H, COOHR

NH

NH

NH

NH

MeO

MeO

R

N

MeO

MeO

N N

N

S

Nucleophilic substitution at the alkenyl and cyclopropyl carbon atoms of magnesium carbenoids: a DFT study pp 5072–5074

Tsutomu Kimura*, Tsuyoshi Satoh

Contents / Tetrahedron Letters 54 (2013) 4991–5000 4995

A simple quinoxaline-based highly sensitive colorimetric and ratiometric sensor, selective for nickel andeffective in very high dilution

pp 5075–5077

Shyamaprosad Goswami*, Shampa Chakraborty, Sima Paul, Sandipan Halder, Annada C. Maity

Synthesis of molecular scaffolds assimilating both indolinone and thiazolidinone moieties under environmentallybenevolent conditions

pp 5078–5082

Suman Ray, Chhanda Mukhopadhyay*

S NH

O

S

NH

SiO2 OOO Si S

N

H2O (2 ml) + EtOH (2 ml)Reflux

N

O

O

R1

S N

ON

O

R1

N

Basic ionic liquid promoted heterocyclization to access fused imidazopyridines pp 5083–5086

I. R. Siddiqui*, Shireen, Shayna Shamim, Malik Abdul Waseem, Afaf A. H. Abumhdi, Arjita Srivastava, Anjali Srivastava

N N

H2N [bmIm]OH

r.t., 2-5h N N

N

RRO

O

75-89%

Microwave assisted water mediated benzylic C–H functionalization of methyl aza-arenes and nucleophilicaddition to aromatic aldehydes

pp 5087–5090

N. Nageswara Rao, H. M. Meshram*

N N

OH

R4R4

CHO

R3R3

H2O, MWI

105 0C, 18-40 min

R1

R2

R1

R2

R1 = H, Br, NO2, OMe

R2 = H, NO2

R3 = H, OMe, NO2

R4 =H, OMe, F, Cl, Br, CN, NO2

4996 Contents / Tetrahedron Letters 54 (2013) 4991–5000

Nickel-catalyzed decarboxylative cycloaddition of isatoic anhydrides with alkenes pp 5091–5095

Meng Sun, Yan-Na Ma, Ya-Min Li, Qiu-Ping Tian, Shang-Dong Yang*

N

O

O

OR1

+

NiCl2(PMe3)2 (10 mol %)Zn dust (5 eq.)

toluene, 100 oC, 12 hN

O

R1

R RR2

R3

R2

R3

Asymmetric total synthesis of Tofacitinib pp 5096–5098

Adolfo Maricán, Mario J. Simirgiotis, Leonardo S. Santos*

NO

OH

H

2

N

OH

Boc

6b

N

N

NHMe

NH

7

N

NMe

N

N NH

CN

O

1

In situ slow release of isocyanates: synthesis and organocatalytic application of N-acylureas pp 5099–5102

Atul K. Singh, Ruchi Chawla, Lal Dhar S. Yadav*

R1

O

NH2

TsNBr2

K2CO3, EtOAc, rt NH

NH

R2H2N R2

O

yield 67-94%

O

Ar

ArNu

NuAr

OH

NuH

OH

O OR1

Unprecedented base-promoted nucleophilic addition of diazoesters to nitrones pp 5103–5105

Evelyn Lieou Kui, Alice Kanazawa*, Jean-François Poisson, Sandrine Py*

R1 R2

NR3O

OR4

N2

O

R1 OR4

N

N2

O

R2

HO R3

THF, −78 °C

46−100%, 15 examples

+ LiHMDS

dr 60:40 to > 99:1

Contents / Tetrahedron Letters 54 (2013) 4991–5000 4997

Network of carboxypyranomalvidin-3-O-glucoside (vitisin A) equilibrium forms in aqueous solution pp 5106–5110

Joana Oliveira, Nuno Mateus, Victor de Freitas*

Synthesis of novel 2H,8H-pyrano[2,3-f]chromene-2,8-diones from 8-formyl-7-hydroxy-4-methylcoumarin pp 5111–5114

Ahmed Al-Kawkabani, Baya Boutemeur-Kheddis*, Malika Makhloufi-Chebli, Maamar Hamdi, Oualid Talhi, Artur M. S. Silva*

OHO

O

O

CH3

OO

O

O

CH3

R

Knoevenagel CyclisationHydrolysis

Activated methylene

A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones

pp 5115–5117

Antonio Guirado*, Enrique Alarcón, Yesica Vicente, Raquel Andreu

Ar1

O

CCl3

Ar2

NH

NH2+ HN N

Ar2

Ar1

HO

CCl3

N NH

Ar2

Ar1 CCl3

HCeneuloT 2Cl2 , H2SO4 THF, t-BuOK N N

Ar2

Ar1

CH3CN, K2CO3N N

Ar2

Ar1

one-pot

p-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: a versatile reagent for mild acid catalyzed etherification pp 5118–5121

Nadine Barroca-Aubry*, Mohamed Benchekroun, Filipe Gomes, David Bonnaffé

4998 Contents / Tetrahedron Letters 54 (2013) 4991–5000

Immobilised Candida antarctica B as efficient catalyst for the synthesis of local anaesthetic intermediates pp 5122–5125

Daniela Giunta, Maria Paola Masia, Mauro Marchetti, Raffaele Morrone, Maurizio Solinas*

O OH

R1R2

+ HOR3

O O

R1R2

R3

+ H2O

R1 ,R2 = H, CH3, iPr, Cl, NO2, CF3 ...R3 = H, C5H11, N(CH2CH3)2

cyclohexane40 - 80 °C

Up to quantitative yields

Novozym 435

20 - 24 hours

A facile access to substituted indoles utilizing palladium catalyzed annulation under microwave enhancedconditions

pp 5126–5129

Ranjith P. Karuvalam, Karickal R. Haridas*, Ayyiliath M. Sajith, Arayambath Muralidharan

N

R3

R2N

I

HR3

O+ PdCl2/(A-taphos)

1(a-q) 3(a-q)2(a-q)H

R2R1 R1

Cesium acetateDioxane

microwave, 120 oC

A highly active and efficient catalytic system PdCl2/A-taphos was employed for the synthesis of indoles via palladium catalyzed ring annulation of ortho iodoanilines and aldehydes.

Selective deprotection of TBDMS alkyl ethers in the presence of TIPS or TBDPS phenyl ethers by catalytic CuSO4Æ5H2Oin methanol

pp 5130–5132

Davir González-Calderón*, Luis J. Benítez-Puebla, Carlos A. González-González, Salomón Assad-Hernández,Aydeé Fuentes-Benítez, Erick Cuevas-Yáñez, David Corona-Becerril, Carlos González-Romero*

OR

TBDMSO

OR

HOMW or

20 mol%CuSO4 5H2O

MeOH

R= TIPS or TBDPS

Development of one-pot synthesis of a-hydroxy a-trifluoromethyl amides pp 5133–5136

Zhaoyang Meng*, William E. Butcher

X

1. iPrMgCl, 0 oC

2.F3C

OOMe

O, -78 oC

3. iPrMgcl, HNR2

R1, 0 oC -> rt

F3C

OHN

OR2

R1R

R

one-pot synthesis

Contents / Tetrahedron Letters 54 (2013) 4991–5000 4999

An unexpected one step domino conversion of TMS-alkynes to protected ketones in 4-chromenone system pp 5137–5139

Prabuddha Bhattacharya, Amit Basak*

O

O TMSKF/CH3CN

O

Od4-MeOH O

OCD3

OCD3

OCD3

Calculated mass MNa+: 266.1355 Found: 266.1396

O

OCD3

O Calculated mass MH+: 192.0740 Found: 192.0781

O

O

R

TMS

O

O

R MeOO

82-85%

i i = Ethylene glycol:MeOH 5:1, 45 oC, 16-18 h

5 examples

OTHER CONTENT

Erratum to ‘‘Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reactionprogress by an increase in fluorescence’’ [Tetrahedron Lett. 54 (2013) 4306–4308]

p 5140

Nobuyuki Mase*, Kunihiko Takabe, Fujie Tanaka*

*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�

Available online at www.sciencedirect.com

ScienceDirect ISSN 0040-4039

5000 Contents / Tetrahedron Letters 54 (2013) 4991–5000