Tetrahedron 70 (2014) 1703e1707

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Tetrahedron

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

Tetrahedron Vol. 70, Issue 9, 2014

Contents

REPORT

Application of CuAAC for the covalent immobilization of homogeneous catalysts

pp 1709e1731 Antony E. Fernandes*, Alain M. Jonas, Olivier Riant*

ARTICLES

Microwave-assisted selective and efficient synthesis of 1,3,5-triazinyl mono and bisureas

pp 1733e1739 Amparo Ruiz-Carretero, Jos�e Ram�on Ramírez, Ana S�anchez-Migall�on*, Antonio de la Hoz*

Contents / Tetrahedron 70 (2014) 1703e17071704

One-pot synthesis of sulfonyl (E)-stilbenes by nitrobenzene-mediated dimerizative desulfonation of benzylic sulfones pp 1740e1747

Meng-Yang Chang*, Yi-Chia Chen, Shin-Ying Lin, Chieh-Kai Chan

SO NaH, THF

PhNO2O Tol SO

O Tol

3a 4a (86%)

hv, I2, EtOAcSO

O Tol

6a (72%)

2

Construction of polyaromatics via photocyclization of 2-(fur-3-yl)ethenylarenes, using a 3-furyl group as an isopropenyl pp 1748e1762

equivalent synthon Ying-Zhe Chen, Ching-Wen Ni, Fu-Lin Teng, Yi-Shun Ding, Tunng-Hsien Lee, Jinn-Hsuan Ho*

R

X

R

X = -CH=CH-O, S

RRR

R = CH3 under KOH/CH3OH (18 examples)R = CH2CH2OH under LiBH4/CH3OH (13 examples)

A BA = no -CH2-

-CH2-B = -CH2CH2-

-CH2CH2CH2-

Ar

substitutedarenes O

Ar

substitutedarenes:

A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from pp 1763e1772

arylboronic acids in ethanol at room temperature Amit Kumar, Sangit Kumar*

E) + BOH

OH

E

R/XX/R

R = CH , CF , NH , OCH , F, Cl, Br, CN, NO COOH, COCH

E = Te, 21 examples (40-98% yields)E = Se, 20 examples (46-96% yields)E = S, 9 examples (68-86% yields)Symmetrical selenides 8 examples (61-93%yields)

CuSO .5H O, L, NaBHO / air, 5-8h, Ethanol,

room tempeature

Two lignans, one alkaloid, and flavanone from the twigs of Feroniella lucida pp 1773e1779

Teerayut Sriyatep, Suda Chakthong*, Sukanlaya Leejae, Supayang P. Voravuthikunchai

Contents / Tetrahedron 70 (2014) 1703e1707 1705

A four-component synthesis of novel spiro[pyrazoloquinoline-oxindoles] under solvent-free conditions pp 1780e1785

Hamide Hosseinjani-Pirdehi, Kurosh Rad-Moghadam*, Leila Youseftabar-Miri

p-TSA

80 °C

R= Me, iPr, Ph Z = H, NO2, CH3O, Cl 4a-h or 7a-bYields 53-92 % 78-81 %

NH

O

OZ

HNN

N

NHOZ

R

O O

OEt

PhHN NH2

NH2

Ph

R

HNN

N

NHOZ

Ph

R

Enantioselective oxidative-coupling of polycyclic phenols pp 1786e1793

Shinobu Takizawa, Junpei Kodera, Yasushi Yoshida, Makoto Sako, Stefanie Breukers, Dieter Enders, Hiroaki Sasai*

Reactions of vinyl sulfone with a-diazo-b-ketosulfone and BestmanneOhira reagent for the regioselective synthesis of pp 1794e1799

highly functionalized pyrazoles Rahul Kumar, Deepa Nair, Irishi N.N. Namboothiri*

Direct synthesis of the arylboronic acid analogues of phenylglycine via microwave-assisted four-component Ugi pp 1800e1804

reaction Ru-Ching Lian, Meng-Hsuan Lin, Pin-Hsuan Liao, Jia-Jie Fu, Meng-Ju Wu, Yang-Chang Wu, Fang-Rong Chang, Chin-Chung Wu,Po-Shen Pan*

In this study, an Ugi four-component reaction (Ugi-4CR) utilizing unprotected boronic acid building blocks under mild condition is developed.The described reactions were performed in methanol and accelerated by employing microwave irradiation. This strategy allows the direct generationof boronic acid analogs without protection and deprotection operations of boronic acid moiety, making it suitable for the preparation ofboron-containing chemical libraries. The synthesized boronic acid analogs were subsequently evaluated for their cytotoxic activity by the MTT assay.Two potential lead compounds were found to be cytotoxic against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potentialapplication of this approach in developing novel boron-containing pharmaceuticals.

Contents / Tetrahedron 70 (2014) 1703e17071706

A novel one-pot synthesis of carbazole-1,4-quinones through Pd-catalyzed cyclocarbonylation, desilylation and pp 1805e1810

oxidation processes from 3-iodo-2-propenylindoles Mami Fujii, Takashi Nishiyama, Tominari Choshi*, Nanase Satsuki, Takaya Fujiwaki, Takumi Abe, Minoru Ishikura, Satoshi Hibino*

N

O

OMOM

R1

R2

N

I

OTBSMOM

R1

R2 1)

CO (1 atm)PdCl2(dppf)

2) TBAF, O2

SnBu3

Isolable atropisomers of 2-aryl indoline derivatives: determination of rotational barrier by density functional theory pp 1811e1817

approach Masashi Eto*, Koki Yamaguchi, Akiko Watanabe, Kazunobu Harano

Solvent-free Brønsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols pp 1818e1826

Margherita Barbero*, Silvano Cadamuro, Stefano Dughera, Marta Rucci, Giulia Spano, Paolo Venturello

A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and regioselectivity via a simple and efficient alkylation of aromaticcompounds through direct SN1-type alcohol nucleophilic substitution in the presence of o-benzenedisulfonimide under neat conditions.

Novel chiral bifunctional L-thiazoline-amide derivatives: design and application in the direct enantioselective aldol pp 1827e1835

reactions Zhiyong Gong, Chiyu Wei, Ye Shi, Qingchuan Zheng, Zhiguang Song*, Zaiqun Liu

Contents / Tetrahedron 70 (2014) 1703e1707 1707

Selective functionalization of 2-oxoallobetulin derivatives pp 1836e1840

Thuc Dinh Ngoc, Wim Dehaen*

CORRIGENDUM

Corrigendum to “Energy level tunable pre-click functionalization of [60]fullerene for nonlinear optics”[Tetrahedron 70 (2014) 573e577]

p 1841

Wan-Shu Zhang, Dong Wang*, Hui Cao, Huai Yang*

*Corresponding authorSupplementary data available via ScienceDirect

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ISSN 0040-4020