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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 10
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Abstracts

Graphical Abstracts

Pages i-vii | Published online: 16 Aug 2006
 

Abstract

Synth. Commun. 2005, 35, 1285

Chemoselective Formation of 8,9‐Epoxy‐limonene

Queli A. R. Almeida and Joel Jones Jr.

Síntese Orgânica Ambiental, Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil

We present here a synthetic path to produce, exclusively, 1:1 mixture of 8,9‐epoxy‐limonenes (I) in 75% overall yields, >99% purity without any trace of 1,2‐epoxide‐limonenes.

Abstract

Synth. Commun. 2005, 35, 1291

Regioselective Synthesis of Coumarin and Quinolone‐Annulated Spiro Heterocycles via Aryl Radical Cyclization

K. C. Majumdar, P. P. Mukhopadhyay, and P. K. Basu

Department of Chemistry, University of Kalyani, Kalyani, India

Abstract

Synth. Commun. 2005, 35, 1301

Lithium Chloride–Assisted Chemoselective Conversion of Aldehydes into Geminal Diacetates under Solvent‐Free Conditions

J. W. John Bosco, N. Purkayastha, B. Rama Raju, and Anil K. Saikia

Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, India

It has been observed that lithium chloride and acetic anhydride could be used for the conversion of aldehydes into geminal diacetates under solvent‐free conditions in high yields. Ketones and other protecting groups such as TBDMS, THP, thioethers, and methoxy are not affected under these reaction conditions.

Abstract

Synth. Commun. 2005, 35, 1307

Silica Sulphuric Acid: An Efficient and Recyclable Catalyst for the Synthesis of β‐Acetamido Ketones in Single Pot

T. Yakaiah, G. Venkat Reddy, B. P. V. Lingaiah, B. Narsaiah, and P. Shanthan Rao

Fluoroorganic Division, Indian Institute of Chemical Technology, Hyderabad, India

Abstract

Synth. Commun. 2005, 35, 1313

Regioselective Iodination of Activated Arenes using Phenyl Trimethylammonium Dichloroiodate in Ionic Liquid under Microwave Irradiation

Rutuja D. Tilve and Vinod R. Kanetkar

Dyestuff Technology Division, Institute of Chemical Technology, University of Mumbai, Matunga, Mumbai, India

Abstract

Synth. Commun. 2005, 35, 1319

Triphenyl Phosphonium Perchlorate–Catalyzed Imino Diels–Alder Synthesis of Azabicyclo[2.2.2]octan‐5‐ones

Gnanamani Shanthi and Paramasivan T. Perumal

Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai, India

Abstract

Synth. Commun. 2005, 35, 1329

Simple, Extremely Fast, and High‐Yielding Oxidation of Thiols to Disulfides

Ashraful Alam, Yutaka Takaguchi, and Sadao Tsuboi

Department of Environmental Chemistry and Materials, Okayama University, Okayama, Japan

Simple addition of 0.20–0.25 mol equiv. of 1,3‐dibromo‐5,5‐dimethylhydantoin (DBDMH) to thiols in CHCl3 at rt yielded about 100% disulfides within 20 sec∼3 min. No other oxidized side products have been found to be formed.

Abstract

Synth. Commun. 2005, 35, 1335

Debromination of α‐Bromoketones and vic‐Dibromides Using Indium in the Presence of Carboxylic Acid

Seung Hwan Lee,1 Min Young Cho,2 Mi Hye Nam,2 Young Sang Park,1 Byung Woo Yoo,2 Chi‐Woo Lee,2 and Cheol Min Yoon2

1Graduate School of Biotechnology and 2Department of Advanced Material Chemistry, Korea University, South Korea

The debromination of α‐bromoketones and vic‐dibromides using indium metal in the presence of acetic acid at room temperature effectively afforded the corresponding ketones in excellent yield.

Abstract

Synth. Commun. 2005, 35, 1343

Synthesis and Characterization of Sulfonyl‐Functionalized Ionic Liquids

Zhengyin Du, Zuopeng Li, and Youquan Deng

Centre for Green Chemistry and Catalysis, Lanzhou Institute of Chemical Physics, Chinese Academy of Science & Graduate School of the Chinese Academy of Sciences, Lanzhou, China

Novel sulfonyl‐functionalized ionic liquids (SFIL) with –SO3H and –SO2Cl groups have been designed, synthesized, and characterized.

Abstract

Synth. Commun. 2005, 35, 1351

Microwave‐Assisted Synthesis of 2‐Amino‐thiophene‐3‐Carboxylic Derivatives under Solvent‐Free Conditions

Wei Huang,1,2 Jian Li,1,2 Jing Tang,1 Hong Liu,1 Jianhua Shen,1 and Hualiang Jiang1

1Drug Discovery and Design Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, China

2Graduate School of the Chinese Academy of Sciences, Shanghai, China

Under microwave irradiation and solvent‐free conditions, cyanoacetates (cyanoacetamides) react with ketones and sulphur in the presence of a small amount of morpholine to give 2‐amino‐thiophene‐3‐carboxylic derivatives. In particular, tetrahydro‐benzo[b]thiophene‐3‐carboxylic acid N‐aryl amides were synthesized in high yields of 84–95%.

Abstract

Synth. Commun. 2005, 35, 1359

PTC‐Promoted Japp–Klingmann Reaction for the Synthesis of Indole Derivatives

Wei He,1 Bang‐Le Zhang,1 Zhong‐Jie Li,2 and Sheng‐Yong Zhang1

1Department of Chemistry, Fourth Military Medical University, Xi'an, Shaanxi, China

2Department of Chemistry, Northwest University, Xi'an, Shaanxi, China

Aryl hydrazones 4 were obtained by PTC‐promoted Japp–Klingmann reaction in yields of more than 90%. Several different phase‐transfer catalysts were investigated and dimethyldioctadecyl ammonium chloride (DMDOA) was found to promote this reaction efficiently. The pure aryl hydrazones were then efficiently cyclized to indole derivatives 5 in yields of more than 80%.

Abstract

Synth. Commun. 2005, 35, 1369

One‐Step Synthesis of 2‐Aryl‐4,5‐Diphenylimidazoles Under Microwave Irradiation

Jian‐Feng Zhou,1,2 Yuan‐Zhi Song,1 Yan‐Ling Yang,1,2 Yu‐Lan Zhu,1,2 and Shu‐Jiang Tu3

1Department of Chemistry, Huaiyin Teachers College, Huaian, China

2Key Laboratory of Low‐Dimensional Materials Chemistry of Jiangsu Province, Huaian, China

3Department of Chemistry, Xuzhou Normal University, Xuzhou, China

A series of 2‐aryl‐4,5‐diphenylimidazoles were synthesized by a one‐step condensation reaction of benzil, aromatic aldehyde, and ammonium acetate in acetic acid under microwave irradiation. The reactions were completed in 4–11 min with good yields and easy workup.

Abstract

Synth. Commun. 2005, 35, 1375

Efficient, Simple Preparation of 1,3‐Diamine Derivatives through Addition of Acrylamides with Secondary Amines

Yi Liu, Ruimano Hua, and Xianqing Qiu

Department of Chemistry, Tsinghua University, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing, China

Abstract

Synth. Commun. 2005, 35, 1381

Microwave‐Promoted Synthesis of 2‐Amino‐4‐aryl‐4H‐pyrans on Soluble Polymeric Support

Min Xia,1 Qiong Chen,2 and Yue‐dong Lu1

1Department of Applied Chemistry, Zhejiang University of Sciences, Hangzhou, China

2Department of Biological and Chemical Engineering, Jiaxing College, Jiaxing, China

Abstract

Synth. Commun. 2005, 35, 1391

A Facile Synthetic Route to Monodisperse Asymmetrical Oligo(phenylene‐ethynylene)s

Jinling Zhao and Zhishan Bo

State Key Laboratory of Polymer Physics and Chemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China

Abstract

Synth. Commun. 2005, 35, 1403

Optical Resolution, Stereoselective Synthesis, and Crystal Structure of 9α‐(3‐Azabicyclo[3,3,1]nonanyl)‐2′‐cyclopentyl‐2′‐hydroxy‐2′‐phenylacetate

Yan‐Qing Liu,1 He Liu,2 Bo‐hua Zhong,2 Yu‐Lin Deng,1 and Ke‐liang Liu2

1School of Life Science and Technology, Beijing Institute of Technology, Beijing, China 2No. 7 Department, Beijing Institute of Pharmacology and Toxicology Academy, Beijing, China

The enantiomers of 9α‐(3‐Azabicyclo[3,3,1]nonanyl)‐2′‐cyclopentyl‐2′‐hydroxy‐2′‐phenylacetate were obtained by optical resolution and an effective diastereoselective synthesized method. Its structure was elucidated by X‐ray analysis.

Abstract

Synth. Commun. 2005, 35, 1413

Convenient Metal‐Free Aziridination of Alkenes with Chloramine‐T Using Tetrabutylammonium Iodide in Water

Hugjiltu Wu, Li‐Wen Xu, Chun‐Gu Xia, Jin Ge, and Lei Yang

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences and Graduate School of the Chinese Academy of Sciences, Lanzhou, China

Tetrabutylammonium iodide was found to be a mild and efficient catalyst for aziridinaton of olefins with Chloramines‐T under environment benign conditions.

Abstract

Synth. Commun. 2005, 35, 1419

Magnesium‐induced Pinacol Coupling of Aromatic Aldehydes and Ketones Under Ultrasound Irradiation

Jian‐Sen Wang,1,2 Ji‐Tai Li,1 Zhi‐Ping Lin,1 and Tong‐Shuang Li1

1College of Chemistry and Environmental Science, Hebei University, Key Laboratory of Analytical Science and Technology, Hebei Province, Baoding, China

2Department of Chemistry, Handan Normal College, Handan, China

The system of magnesium and magnesium iodide can reduce some aromatic aldehydes and ketones to the corresponding pinacols in good yields within 10–60 min at room temperature under ultrasound irradiation.

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