Graphical Abstracts

Abstract

Graphical Abstract Section

Abstract

Synth. Commun. 2007, 37, 4289

SYNTHESIS OF CHIRAL BENZIMIDAZOLE‐PYRROLIDINE DERIVATIVES AND THEIR APPLICATION IN ORGANOCATALYTIC ALDOL AND MICHAEL ADDITION REACTIONS

K. Rajender Reddy, G. Gopikrishna, and C. V. Rajasekhar

Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, India

Abstract

Synth. Commun. 2007, 37, 4301

L‐PROLINE‐CATALYZED ASYMMETRIC DIRECT ALDOL REACTION OF HETERO‐AROMATIC ALDEHYDES AND ACETONE: HIGHER SELECTIVITY IN ROOM TEMPERATURE IONIC LIQUID BMIM [BF₄]

K. Rajender Reddy, L. Chakrapani, T. Ramani, and C. V. Rajasekhar

Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, India

Abstract

Synth. Commun. 2007, 37, 4309

CYCLOPENTYL: A NOVEL PROTECTIVE GROUP FOR PHENOLS

Jitendra M. Gajera, Laxmikant A. Gharat, and Aniket V. Farande

Drug Discovery Chemistry, Glenmark Research Centre, Maharashtra Industrial Development Corporation, Mumbai, India

Utility of cyclopentyl as a novel protective group for phenol is described. Removal of the cyclopentyl group using hydrobromic acid is also demonstrated.

Abstract

Synth. Commun. 2007, 37, 4313

FIRST TOTAL SYNTHESIS OF BAUERINE C

Y. Lingam,¹ D. Muralimohan Rao,² Dipal R. Bhowmik,¹ and Aminul Islam¹

¹Custom Pharmaceutical Services, Dr. Reddy's Laboratories Limited, Hyderabad, India

²College of Engineering, Jawaharlal Nehru Technological University, Kakinada, Andhra Pradesh, India

The first total synthesis of Bauerine C, a unique indoloquinazoline alkaloid, has been achieved from readily available 2,3‐dichloroaniline. The key step is the Japp–Klingmann condensation between 2,3‐dichloroaniline and ethyl‐2‐acetyl‐5‐phthalimido pentanoate to get 3‐[(2,3‐dichlorophenyl)‐hydrozono]‐pipiridin‐2‐one, which cyclizes to 7,8‐dichloro 2,3,4,9‐tetrahydro‐β‐carbolin‐1‐one which can be methylated by dimethyl sulphate to give 7,8-dichloro‐9‐methyl 2,3,4,9‐tetrahydro‐β‐carbolin‐1‐one. This N‐methyl derivative is then subjected to dehydrogenation with DDQ to give the desired compound Bauerine C.

Abstract

Synth. Commun. 2007, 37, 4319

LIBR-CATALYZED SIMPLE AND EFFCIENT SYNTHESIS OF SOME NOVEL SUBSTITUTED QUINOLINES VIA FRIEDLANDER HETEROANNULATION REACTION

M. A. Päsha, K. A. Mahammed, and V. P. Jayäshankara

Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India

A simple and effcient method has been developed for the condensation of o‐aminoaryl ketones with α‐methylene ketones in the presence of catalytic amounts of LiBr to afford the corresponding fused cyclic quinolines in high yield using the Friedlander heteroannulation reaction. The reaction works at ambient temperature to give the products within 1.5–2 h.

Abstract

Synth. Commun. 2007, 37, 4327

IODINE‐CATALYZED, ONE‐POT SOLID-PHASE SYNTHESIS OF BENZOTHIAZOLE DERIVATIVES

Sayan Dutta Gupta, Hemendra Pratap Singh, and N. S. Hari Narayana Moorthy

School of Pharmaceutical Sciences, Rajiv Gandhi Proudyogiki Vishwavidyalaya, Bhopal, Madhya Pradesh, India

Molecular iodine was utilized for a one‐pot, solid‐phase reaction between 2‐amino thiophenol and benzoic acid derivatives to yield highly economic benzothiazole derivatives.

Abstract

Synth. Commun. 2007, 37, 4331

SYNTHESIS OF THIAZOLES AND AMINOTHIAZOLES FROM β‐KETO TOSYLATES UNDER SUPRAMOLECULAR CATALYSIS IN THE PRESENCE OF β‐CYCLODEXTR INWATER

V. Pavan Kumar, M. Narender, R. Sridhar, Y. V. D. Nageswar, and K. Rama Rao

Organic Chemistry Division I, Indian Institute of Chemical Technology, Hyderabad, India

Abstract

Synth. Commun. 2007, 37, 4337

SYNTHESIS AND CHARACTERIZATION OF RELATED COMPOUNDS OF ARIPIPRAZOLE, AN ANTIPSYCHOTIC DRUG SUBSTANCE

T. Poorna Chander, B. Satyanarayana, N. Ramesh Kumar, P. Pratap Reddy, and Y. Anjaneyulu

Research and Development Centre, Dr. Reddy's Laboratories Limited, Hyderabad, AP, India and Institute of Science and Technology, JNTU, Hyderabad, India

Abstract

Synth. Commun. 2007, 37, 4343

SYNTHESIS OF N‐PROTECTED/FREE INDOLE‐7‐CARBOXALDEHYDE

Arasambattu K. Mohanakrishnan, Ramalingam Balamurugan, Neelamegam Ramesh, Manoharan Mathiselvam, and Subramaniam Manavalan

Department of Organic Chemistry, University of Madras, Chennai, India

Abstract

Synth. Commun. 2007, 37, 4353

MOLECULAR IODINE: AN EFFCIENT CATALYST FOR THE SYNTHESIS OF TETRAHYDROBENZO[B]PYRANS

Rajesh S. Bhosale, Chandrakant V. Magar, Kuldeep S. Solanke, Sandeep B. Mane, Sunil S. Choudhary, and Rajendra P. Pawar

Organic Chemistry Synthesis Laboratory, Dnyanopasak College, Parbhani, India

An iodine/DMSO system is introduced as an excellent catalyst in three‐component coupling reactions of tetrahydrobenzo[b]pyran synthesis. The reaction proceeds quickly under very mild reaction conditions.

Abstract

Synth. Commun. 2007, 37, 4359

NOVEL PROCEDURE FOR THE SYNTHESIS OF 1-HYDROXY-1,1 BISPHOSPHONIC ACIDS USING PHENOL(S) AS MEDIUM

Divvela V. N. Srinivasa Rao,¹ Ramesh Dandala,¹ Garimella K. A. S. S. Narayanan,¹ Racha Lenin,¹ M. Sivakumaran,¹ and Andra Naidu²

¹Research and Development Department, Aurobindo Pharma Ltd, 313, Bachupally, Hyderabad, Andhra Pradesh, India

²Jawaharlal Nehru Technological University, Kukatpally, Hyderabad, India

Abstract

Synth. Commun. 2007, 37, 4367

CYANURIC CHLORIDE–MEDIATED SYNTHESIS OF ALLYLIC CHLORIDE–IPSO VERSUS TELE‐SUBSTITUTION

Sanchita Roy, Tarak Das, Manabendra Saha, Subrata Kumar Chaudhuri, and Sanjay Bhar

Department of Chemistry, Organic Chemistry Section, Jadavpur University, Kolkata, India

Abstract

Synth. Commun. 2007, 37, 4371

CERIUM(III) CHLORIDE: A HIGHLY EFFCIENT REAGENT FOR THE SYNTHESIS OF α‐AMINONITRILES

M. A. Pasha, H. M. Nanjundaswamy, and V. P. Jayashankara

Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India and Chemical Examination Section, Public Health Institute, Bangalore, India

We report a highly eFFcient, one‐pot, three‐component condensation of carbonyl compounds, amines, and TMSCN in MeCN; the reaction is significantly promoted by the catalytic amount of cerium(III) chloride at ambient temperature in excellent yields without any adverse effect on the other substituents. The method afforded an elegant alternative to the synthesis of α‐aminonitriles. The reactions are fast and clean, and the products obtained are of high purity.

Abstract

Synth. Commun. 2007, 37, 4381

DEVELOPMENT OF A PRACTICAL AND SCALABLE PREPARATION USING SONICATION OF PD/FIBROIN CATALYST FOR CHEMOSELECTIVE HYDROGENATION

Yoshiaki Kitamura,¹ Asami Tanaka,¹ Mutsumi Sato,² and Keiji Oono,² Takashi Ikawa,¹ Tomohiro Maegawa,¹ Yasunari, Monguchi,¹ and Hironao Sajiki¹

¹Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora‐higashi, Gifu, Japan

²Reagent Research Laboratories, Wako Pure Chemical Industries, Ltd., Matoba, Kawagoe, Saitama, Japan

Abstract

Synth. Commun. 2007, 37, 4389

SM/HOAC/ETOH SYSTEM–MEDIATED REDUCTION OF BAYLIS‐HILLMAN ACETATES

Yunkui Liu,¹ Dajie Mao, Danqian Xu,¹ Zhenyuan Xu,¹ and Yongmin Zhang²

¹State Key Laboratory Breeding Base of Green Chemistry—Synthesis Technology, Zhejiang University of Technology, Hangzhou, China

²Department of Chemistry, Zhejiang University, Hangzhou, China

Abstract

Synth. Commun. 2007, 37, 4399

EFFICIENT SELECTIVE FORMATION OF C‐C SINGLE BONDS AND C˭C DOUBLE BONDS BY NBS-PROMOTED OXIDATIVE COUPLING OF β‐KETO ESTERS

Zhiguo Wang, Guodong Yin, Aihua Chen, Shengli Hu, and Anxin Wu

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan China

Abstract

Synth. Commun. 2007, 37, 4407

EFFICIENT MICROWAVE‐ASSISTED SYNTHESIS OF 9,9‐BIS[4‐(2‐HYDROXYETHOXY)PHENYL]FLUORENE FROM 9‐FLUORENONE AND 2‐PHENOXYETHANOL

Kazuaki Hiroki, Nahoko Morii, Hiroshi Yamashita, and Jun‐ichi Sugiyama

National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan

9‐Fluorenone (1) smoothly reacts with phenoxyethanol (2) in the presence of Al³⁺‐motmorillonite catalyst and 3‐mercaptopropionic acid as a cocatalyst under microwave irradiation at 160°C for 10 min to give 9,9‐bis[4‐(2‐hydroxyethoxy)phenyl]fluorene (3) in 81% yield.

Abstract

Synth. Commun. 2007, 37, 4415

MICROWAVE‐ASSISTED RAPID AND STRAIGHTFORWARD SYNTHESIS OF NOVEL 6‐(AROXYMETHYL)‐2‐ARYL‐6,7‐DIHYDROPYRAZOLO[5,1‐C][1,4]OXAZIN‐4‐ONE DERIVATIVES

Fang Wei,¹ Bao‐Xiang Zhao,¹ Wen‐Liang Dong,¹ Hua Zuo,² Dong‐Soo Shin,² Da‐Wei Wang,³ Yong Xia,¹ and Yan‐Qing Ge¹

¹Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan, China

²Department of Chemistry, Changwon National University, Changwon, Korea

³Shandong Center for Disease Control and Prevention, Jinan, China

A series of novel 6‐(aroxymethyl)‐2‐aryl‐6,7‐dihydropyrazolo[5,1‐c][1,4]oxazin‐4‐one derivatives was synthesized from ethyl 3‐aryl‐1H‐pyrazole‐5‐carboxylate and 2‐aryloxymethylepoxide by a microwave‐assisted, one‐step method in good yields. The microwave‐assisted reaction of ethyl 3‐aryl‐1H‐pyrazole‐5‐carboxylate and 2‐aryloxymethylepoxide proceeds with higher resioselectivity and is more economical and environmentally friendly in contrast to the normal intramolecular esterification route. A tandem mechanism of the reaction was proposed.

Abstract

Synth. Commun. 2007, 37, 4425

FECL₃‐CATALYZED AZA‐DIELS–ALDER REACTIONS OF METHYLENECYCLOPROPANES WITH IMINES

Ke Gao, Yizhe Li, Huixia Sun, Renhua Fan, and Jie Wu

Department of Chemistry, Fudan University, Shanghai, China

Abstract

Synth. Commun. 2007, 37, 4439

Y(OTF)₃‐CATALYZED, ONE‐POT SYNTHESIS OF 1,2,4‐OXADIAZOLE DERIVATIVES

Chuanming Yu, Min Lei, Weike Su, and Yuanyuan Xie

College of Pharmaceutical Sciences, Zhejiang University of Technology, Zhejiang Key Laboratory of Pharmaceutical Engineering, Hangzhou, China

Direct one‐step synthesis of 1,2,4‐oxadiazole from ketones, nitriles, and nitric, acid is described using yttrium triflate [Y(OTf)₃] as the catalyst. The salient features of this method include a simple procedure, mild condition easy purification, and good yields.