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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Abstracts

Graphical Abstracts

Pages 2103-2110 | Published online: 03 Jul 2007
 

Abstract

Graphical Abstract Section

Synth. Commun. 2007, 37, 2111

D,L‐PROLINE‐CATALYZED ONE‐POT SYNTHESIS OF PYRANS AND PYRANO[2,3‐C]PYRAZOLE DERIVATIVES BY A GRINDING METHOD UNDER SOLVENT‐FREE CONDITIONS

Shao‐Bo Guo, Shu‐Xiang Wang, and Ji‐Tai Li

College of Chemistry and Environmental Science, Hebei University, Baoding, China

D,L‐Proline was found to efficiently catalyze the one‐pot condensation of aromatic aldehydes, malononitrile, and dimedone (1,3‐cyclohexanedione or 3‐methyl‐1‐phenyl‐2‐pyrazolin‐5‐one). 2‐Amino‐3‐cycano‐4‐aryl‐7,7‐dimethyl‐5,6,7,8‐tetra‐hydrobenzo[b]pyrans and 6‐amino‐5‐cyano‐4‐aryl‐1,4‐dihydropyrano[2,3‐c] pyrazoles were synthesized by a one‐pot grinding reaction under solvent‐free conditions. The reaction proceeded cleanly at room temperature to afford the products in good yields.

Synth. Commun. 2007, 37, 2121

PALLADIUM‐CATALYZED ENYNE CYCLIZATION OF 2′‐ALKENYL 2‐ALKYNOATES IN IMIDAZOLIUM‐TYPE IONIC LIQUIDS

Shaorong Yang, Huanfeng Jiang, Huoji Chen, Yanbin Xu, and Wei Luo

College of Chemistry, South China University of Technology, Guangzhou, China

The palladium(II)‐catalyzed enyne cyclization of 2′‐alkenyl 2‐alkynoates in imidazolium‐type ionic liquids has been investigated. The ionic liquid–catalyst mixture could be recycled several times without an obvious loss of catalytic activity.

Synth. Commun. 2007, 37, 2131

ONE‐POT SYNTHESIS OF 2‐ARYLTHIO‐2‐CYCLOHEXENONE DERIVATIVES BY THE DIELS–ALDER REACTION OF 4‐ARYLTHIO‐3‐HYDROXY‐2‐PYRONES

Takuzo Komiyama, Yutaka Takaguchi, and Sadao Tsuboi

Department of Material and Energy Science, Graduate School of Environmental Science, Okayama University, Okayama, Japan

Synth. Commun. 2007, 37, 2137

FACILE SYNTHESIS OF ISOQUINOLINES, β‐CARBOLINES, AND 3‐DEAZAPURINES

Wenhua Huang, Jingyi Li, and Lihua Ou

Department of Chemistry, Tianjin University, Tianjin, China

Synth. Commun. 2007, 37, 2145

SYNTHESIS OF NOVEL PYRROLO[1′,5′‐a]‐1,8‐NAPHTHYRIDINE DERIVATIVES THROUGH A FACILE ONE‐POT PROCESS

Xi‐Juan Zhao,1,3 Yong Chen,1,3 Wen‐Fu Fu,1,2,3 and Jia‐Bing Zhang2

1Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, China

2College of Chemistry and Engineering, Yunnan Normal University, Kunming, China

3Graduate University of Chinese Academy of Sciences, Beijing, China

Synth. Commun. 2007, 37, 2153

NOVEL CONVENIENT SYNTHESIS OF MITIGLINIDE

Wei Huang and Jun‐Da Cen

Department of Chemistry, Shanghai Institute of Pharmaceutical Industry, Shanghai, P. R. China

(2S)‐4‐[(3aR,7aS)‐octahydro‐2H–isoindol‐2‐yl]‐4‐oxo‐2‐benzyl‐butanoic acid (6) was prepared by selective hydrolysis of ethyl 4‐[(3aR,7aS)‐octahydro‐2H‐isoindol‐2‐yl]‐4‐oxo‐2‐benzyl‐butanoate (5) using α‐chymotrypsin, the latter was prepared by a novel facile route from (3aR, 7aS)‐octahydro‐2H‐isoindole. The overall yield was 25.6%.

Synth. Commun. 2007, 37, 2159

SYNTHESIS OF 2‐SUBSTITUTED 4,5‐DIPHENYLOXAZOLES UNDER SOLVENT‐FREE MICROWAVE IRRADIATION CONDITIONS

Jong Chan Lee, Jang‐Woo Seo, and Jong Wook Baek

Department of Chemistry, Chung‐Ang University, Seoul, South Korea

A new synthetic method for 2‐substituted 4,5‐diphenyloxazoles from the reaction of deoxybenzoin with [hydroxy(tosyloxy)iodo]benzene/nitriles under microwave irradiation is described.

Synth. Commun. 2007, 37, 2163

ENHANCEMENT OF ENANTIOSELECTIVITY IN THE OPTICAL RESOLUTION OF PRIMARY ALCOHOLS WITH MODIFIED CYCLODEXTRIN COLYOPHILIZED LIPASE

Kosei Shioji, Yoshimitsu Kurauchi, Keiko Terada, Yasushi Kodera, and Kentaro Okuma

Faculty of Science, Department of Chemistry, Fukuoka University, Jonan‐ku, Fukuoka, Japan

Synth. Commun. 2007, 37, 2171

SYNTHESIS OF 1‐INDANONES VIA INTRAMOLECULAR CYCLODEHYDRATION OF 3‐ARYLPROPIONIC ACIDS CATALYZED BY HETEROPOLY ACID AS HETEROGENEOUS CATALYST

Kun Lan and Zi‐Xing Shan

Department of Chemistry, Wuhan University, Wuhan, China

Synth. Commun. 2007, 37, 2179

O‐ARYLATION OF CARBOXYLIC ACIDS USING (PHENYL)[2‐(TRIMETHYLSILYL)PHENYL]IODONIUM TRIFLATE AS A PRECURSOR OF ARYNES

Jian Xue1 and Xian Huang1,2

1Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, China

2State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

Synth. Commun. 2007, 37, 2187

FACILE SYNTHESIS OF 2‐SUBSTITUTED 4‐AZAINDOLES

L.‐P. Sun and J.‐X. Wang

Department of Medicinal Chemistry, Chinese Pharmaceutical University, Nanjing, China

Synth. Commun. 2007, 37, 2195

DIRECT AND CONVENIENT METHOD OF REGIOSELECTIVE BENZYLATION OF METHYL α‐D‐GLUCOPYRANOSIDE

Xiaoliu Li, Zhiwei Li, Pingzhu Zhang, Hua Chen, and Shiro Ikegami

Department of Chemistry, Hebei University, Baoding, China

Methyl 2,3,6‐tri‐O‐benzyl‐α‐D‐glucopyranoside (2) was conveniently prepared by the direct and regioselective benzylation of methyl α‐D‐glucopyranoside (1) with benzyl bromide in the presence of the mild base of K2CO3 and KOH (1∶1).

Synth. Commun. 2007, 37, 2203

APPLICATION OF SUZUKI CROSS‐COUPLING REACTION CATALYZED BY LIGANDLESS PALLADIUM CHLORIDE IN THE SYNTHESIS OF LIQUID CRYSTALS

Mei Huang,1 Jianhua Cheng,1 Xiaochun Tao,2 Mingwang Wei,1 and Dong Shen1

1Laboratory of Chemical Physics, East China University of Science and Technology, Shanghai, China

2Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai, China

Highly pure multiring liquid crystals with a biphenyl unit were prepared using a palladium chloride–catalyzed Suzuki cross‐coupling reaction.

Synth. Commun. 2007, 37, 2209

KNOEVENAGEL CONDENSATION OF AROMATIC ALDEHYDES WITH ACTIVE METHYLENE COMPOUNDS USING a CATALYTIC AMOUNT OF IODINE AND K2CO3 AT ROOM TEMPERATURE

Yi‐Ming Ren and Chun Cai

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing, China

Synth. Commun. 2007, 37, 2215

FORMATION OF N‐SULFONYLCARBAMATES FROM EPICHLOROHYDRIN: SYNTHESIS OF POLYFUNCTIONAL OXAZOLIDIN‐2‐ONES

Hamdi Rmedi,1 Mohamed Béji,2 and Ahmed Baklouti1

1Faculty of Sciences of Tunis, Laboratory of Structural Organic Chemistry, University of Tunis—El manar, Tunis, Tunisia

2Preparatory Institute for Engineering studies of Tunis (IPEIT), Tunis, Tunisia

The addition of 3‐methylbut‐2‐enoic acid‐3‐bromo‐2‐hydroxypropyl ester and 1‐bromo‐3‐phenylsulfanyl propan‐2‐ol, to N‐sulfonylisocyanates affords the corresponding bromocarbamates. These are treated with triethylamine to give the corresponding polyfunctional oxazolidin‐2‐ones with good yields.

Synth. Commun. 2007, 37, 2225

MILD AND SELECTIVE NITRATION OF PHENOLS BY ZEOFEN

Mohammad A. Bigdeli,1 Majid M. Heravi,1 and Firouzeh Nemati2

1Faculty of Chemistry, Teacher Training University, Tehran, Iran

2Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, Iran

Synth. Commun. 2007, 37, 2231

GENERAL AND FACILE SYNTHESIS OF 2‐AMINO‐5‐HALOGENPYRIMIDINE‐4‐CARBOXYLIC ACIDS AND THEIR DERIVATIVES

Evgeniy V. Blyumin,1 Hans Neunhoeffer,1 and Yulian V. Volovenko2

1Darmstadt University of Technology, Institute of Organic Chemistry, Darmstadt, Germany

2Kiev Taras Schevchenko University, Chemical Department, Kiev, Ukraine

A general and facile synthesis of substituted 2‐amino‐5‐halogen‐pyrimidine‐4‐carboxylic acids is reported, which gives rise to a variety of new 2‐amino‐pyrimidine derivatives.

Synth. Commun. 2007, 37, 2243

MICROWAVE‐ASSISTED SYNTHESIS OF AZOCALIXARENES

Y. K. Agrawal,1 N. C. Desai,2 and N. D. Mehta2

1Institute of Pharmacy, Nirma University of Science and Technology, Ahmadabad, India

2Department of Chemistry, Bhavnagar University, Bhaunagar, India

Synth. Commun. 2007, 37, 2253

ULTRASOUND‐ASSISTED‐SYNTHESIS OF β‐ENAMINONITRILES IN THE PRESENCE OF BASE

Sachin R. Jagtap, Mayur J. Bhanushali, Nitin S. Nandurkar, and Bhalchandra M. Bhanage

Department of Chemistry, Institute of Chemical Technology, N. M. Parekh Marg, Matunga, Mumbai, India

Synth. Commun. 2007, 37, 2259

UNEXPECTED REGIOSPECIFIC REDUCTION OF THE DOUBLE BOND BY NABH4 IN 2‐(1‐METHYL/1H‐BENZIMIDAZOLE‐2‐YL)‐3‐ARYL‐ACRYLONITRILE

P. K. Dubey and P. V. V. Prasada Reddy

Department of Chemistry, College of Engineering, JNT University, Kukatpally, Hyderabad, India

Synth. Commun. 2007, 37, 2267

NOVEL ONE‐POT SYNTHESIS OF AZIRIDINES CONTAINING SYDNONE MOIETY

N. Satheesha Rai, Balakrishna Kalluraya, and B. Lingappa

Department of Studies in Chemistry, Mangalore University, Mangalagangothri, Karnataka, India

A facile one‐pot synthesis of a series of novel 1,1a‐dihydro‐1‐aryl‐2‐(3‐aryl‐sydnone‐4‐yl)‐azirino[1,2‐a] quinoxalines was described.

Synth. Commun. 2007, 37, 2275

IMPROVED SYNTHESIS OF CEFDINIR AND ITS POLYMORPHIC FORM, AN ANTIBACTERIAL ACTIVE PHARMACEUTICAL INGREDIENT

Korrapati, V. V. Prasada Rao,1 Ramesh Dandala,1 Meenakshisunderam. S. Sivakumaran,1 Ananta Rani,1 and Andra Naidu2

1Research and Development Department, Aurobindo Pharma Ltd, Hydrabad, India

2Jawaharlal Nehru Technological University, Hyderabad, India

This article describes a new procedure for the synthesis of highly pure cefdinir sesquihydrate.

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