Graphical Abstracts

Abstract Graphical Abstract Section Synth. Commun. 2006, 36, 1637 MICROWAVE‐ACCELERATED, THREE‐COMPONENT, ONE‐STEP SYNTHESIS OF 2‐ACYLIMINO‐3‐ARYL‐3H‐THIAZOLINES UNDER SOLVENT‐FREE CONDITIONS Min Xia and Yue‐dong Lu Department of Applied Chemistry, Zhejiang Sci‐Tech University, Hangzhou, China Synth. Commun. 2006, 36, 1645 MILD AND EFFICIENT PROCEDURE FOR THE SYNTHESIS OF 1,5‐BENZODIAZEPINES CATALYZED BY MAGNESIUM PERCHLORATE Zhan‐Hui Zhang, Shu‐Tao Yang, and Jin Lin College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang, China A convenient and efficient method for the synthesis of 1,5‐benzodiazepines by the reaction of o‐phenylenediamines (OPDA) and ketones with hydrogens at α‐position has been developed. The reaction is carried out under solvent‐free conditions at room temperature in the presence of a catalytic amount of magnesium perchlorate. Synth. Commun. 2006, 36, 1655 NOVEL AND EFFICIENT SOLID‐STATE SYNTHESIS OF 3‐ALKYL‐6‐ARYL‐S‐TRIAZOLO[3,4‐B]‐1,3,4‐THIADIAZINE DERIVATIVES Xin‐Ping Hui, Ren‐Zhong Qiao, Peng‐Fei Xu, and Zi‐Yi Zhang State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, China A novel and efficient solid‐state synthesis of s‐triazolo[3,4‐b]‐1,3,4‐thiadiazine derivatives has been reported in excellent yields with short reaction time. Synth. Commun. 2006, 36, 1661 [BPY]HSO4 ACIDIC IONIC LIQUID AS A NOVEL, EFFICIENT, AND ENVIRONMENTALLY BENIGN CATALYST FOR SYNTHESIS OF 1,5‐BENZODIAZEPINES UNDER MILD CONDITIONS Yuying Du, Fuli Tian, and Wenzhi Zhao Department of Chemistry, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, China A novel and simple ionic liquid methodology for the synthesis of 1,5‐benzodiazepines is described. 1‐Butylpyridinium hydrogen sulphate ([BPy]HSO4), an acidic room‐temperature ionic liquid, as a novel and efficient catalyst, was synthesized and used in the preparation of a series of 1,5‐benzodiazepine derivatives by the reaction of o‐phenylenediamine with chalcones under mild conditions. This method is easy, efficient, environmentally friendly, economical, free of toxic catalysts, and has good yields for the formation of 1,5‐benzodiazepines. Synth. Commun. 2006, 36, 1671 STEREOSELECTIVE SYNTHESIS OF (2E,6E,10E)‐GERANYLGERANIOL FROM GERANYLLINALYL ACETATE VIA PALLADIUM‐CATALYZED AMINATION Yoshifumi Yuasa1 and Yoko Yuasa2 1Takasago International Corporation, Kanagawa, Japan 2School of Pharmacy, Tokyo University of Pharmacy and Life Science, Tokyo, Japan Amination of geranyllinalyl acetate 1 with diethylamine and Pd(OAc)2 · 2PPh3 as catalyst gave N,N‐diethylgeranylgeranylamine 3 (E:Z=91:9) in 85%. Amine 3 was treated by ethyl chloroformate followed by KOAc to give geranylgeranyl acetate 2 in 82%. Then 2 was hydrolyzed to afforded geranylgeraniol 4 in 94%. Synth. Commun. 2006, 36, 1679 NEW CATALYTIC METHODS FOR THE PREPARATION OF ACETALS FROM ALCOHOLS AND ALDEHYDES Yonghong Li, Xiaojun Zhang, Tianrui Ren, and Jiaju Zhou State Key Laboratory of Biochemical Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing, China; Graduate University of Chinese Academy of Sciences, Beijing, China Synthesis of product 3 via acetalization reactions with resin‐D72 catalyst: Synth. Commun. 2006, 36, 1687 PRACTICAL SYNTHESIS OF (S)‐(+)‐3‐OCTANOL BY LIPASE‐CATALYZED ENANTIOSELECTIVE ACETYLATION Yoshifumi Yuasa1 and Yoko Yuasa2 1Takasago International Corporation, Kanagawa, Japan 2School of Pharmacy, Tokyo University of Pharmacy and Life Science, Tokyo, Japan (S)‐(+)‐3‐Octanol (S)‐1 was prepared in high enantiomeric excess through catalyzed acetylation of racemic alcohol 1 by using lipase from Candida antarctica (Chirazyme L‐2) in the presence of vinyl acetate in toluene at 30°C. Synth. Commun. 2006, 36, 1695 PRODUCTS OF AN ACETYLATION PROTOCOL ON TWO PENTAALKOXY-NAPHTHALENES Robin G. F. Giles,1 Ivan R. Green,2 and Nestor van Eeden2 1Department of Chemistry, Murdoch University, Murdoch, Australia 2Department of Chemistry, University of the Western Cape, Bellville, South Africa Acetylation of naphthalenes 18 and 19 afforded 20 but not 25. Synth. Commun. 2006, 36, 1715 MICROWAVE‐PROMOTED ULLMANN CONDENSATION OF 2‐AMINOPYRIDINES WITH 2‐CHLOROBENZOIC ACIDS Rolando F. Pellón Comdom, Ana Martín de la Guardia, Maite L. Docampo Palacios, and Miriam Mesa Hernández Centre of Pharmaceutical Chemistry, Havana, Cuba A new efficient synthetic method of microwave‐promoted Ullmann condensation of 2‐aminopyridines with 2‐chlorobenzoic acids to yield various substituted 11H‐pyrido[2,1‐b] quinazolin‐11‐ones in dry media is presented. Results were compared with those obtained following the classical heating. Synth. Commun. 2006, 36, 1721 CONVENIENT ONE‐POT PROCEDURES FOR THE SYNTHESIS OF 2,2′:6′,2″‐TERPYRIDINE Michael W. Cooke, Jianhua Wang, Isabelle Theobald, and Garry S. Hanan Chemistry Department, University of Montréal, Montréal, Québec, Canada Synth. Commun. 2006, 36, 1727 PREPARATION AND DEPROTECTION OF ALDEHYDE DIMETHYLHYDRAZONES Richard J. Petroski USDA, Agricultural Research Service, National Center for Agricultural Utilization Research, Crop Bioprotection Research Unit, Peoria, Illinois, USA Synth. Commun. 2006, 36, 1735 FRAGMENT ASSEMBLY: AN ALTERNATIVE APPROACH TO GENERATING COMPLEX POLYKETIDES Simon J. Shaw, Dan Zhang, Kurt F. Sundermann, and David C. Myles Kosan Biosciences, Hayward, California, USA Synth. Commun. 2006, 36, 1745 FACILE SYNTHESIS OF RHODAMINE ESTERS USING ACETYL CHLORIDE IN ALCOHOL SOLUTION Justin A. Ross,1 Benjamin P. Ross,2 Halina Rubinsztein‐Dunlop,1 and Ross P. McGeary2,3 1Centre for Biophotonics and Laser Science, School of Physical Sciences, Brisbane, Queensland, Australia 2School of Molecular and Microbial Sciences, Brisbane, Queensland, Australia 3School of Pharmacy, University of Queensland, Brisbane, Queensland, Australia Esters (2–7) of rhodamine 110 (1) were conveniently prepared via the addition of acetyl chloride to a solution of the free acid (1) in the appropriate alcohol. Synth. Commun. 2006, 36, 1751 SILICA‐GEL‐SUPPORTED CERIC AMMONIUM NITRATE (CAN): A SIMPLE AND EFFICIENT SOLID‐SUPPORTED REAGENT FOR OXIDATION OF OXYGENATED AROMATIC COMPOUNDS TO QUINONES Mohammed Hashmat Ali, Melinda Niedbalski, Gary Bohnert, and Daniel Bryant Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USA A silica‐gel‐supported heterogeneous ceric ammonium nitrate (CAN) reagent has been developed for oxidizing oxygenated aromatics to quinones in nonaqueous media. The advantages of this procedure include excellent yields, mild reaction conditions, nonaqueous media, short reaction times, and easy product isolation. Synth. Commun. 2006, 36, 1761 OXIDATIVE CLEAVAGE OF OXIMES WITH SILICA‐GEL‐SUPPORTED CHROMIC ACID IN NONAQUEOUS MEDIA Mohammed Hashmat Ali, Stacie Greene, Candace J. Wiggin, and Saira Khan Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri. USA A simple procedure for a clean and high‐yielding oxidative deoximation of benzaldoximes and ketoximes using a silica‐gel‐supported chromic acid reagent has been developed. This solid‐supported reagent allows us to carry out this reaction in nonaqueous dichloromethane reaction media. Synth. Commun. 2006, 36, 1769 OXIDATION OF SULFIDES WITH N‐BROMOSUCCINIMIDE IN THE PRESENCE OF HYDRATED SILICA GEL Mohammed Hashmat Ali, Melanie Hartman, Kimberly Lamp, Chad Schmitz, and Tim Wencewicz Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USA An efficient and highly selective procedure for oxidation of sulfides to sulfoxides with N‐bromosuccinimide (NBS) in the presence of hydrated silica gel has been developed. Hydrated silica gel supplies the water necessary for decomposition of the intermediate bromosulfonium salt to the product, allowing the reaction to employ a nonaqueous media. Also, this procedure has increased the scope of the reaction by oxidizing a wider variety of sulfides, which was not possible until now. Synth. Commun. 2006, 36, 1779 OXIDATION OF SULFIDES WITH PYRIDINIUM TRIBROMIDE IN THE PRESENCE OF HYDRATED SILICA GEL Mohammed Hashmat Ali and Susan Stricklin Department of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri, USA A variety of sulfides have been oxidized to sulfoxides utilizing pyridinium tribromide in the presence of hydrated silica gel in a non‐aqueous media. A combination of pyridinium tribromide and hydrated silica gel releases molecular bromine slowly in the reaction, affecting the oxidation. Hydrated silica gel also promotes decomposition of the bromosulfonium intermediate to the product. This procedure employs non‐aqueous media for the first time in such a reaction. Synth. Commun. 2006, 36, 1787 EFFICIENT SYNTHESIS OF N,N′‐DISUBSTITUTED UREA/THIOUREAS CATALYZED BY IODINE M. A. Pasha and V. P. Jayashankara Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India Iodine is an efficient catalyst for the synthesis of symmetrically N,N′‐disubstituted ureas/thioureas by heating respective amines or phenyl hydrazine and urea/thiourea on a preheated hot plate at 90–95°C, under solvent‐free conditions. The yields are excellent, and the reactions complete within 5–10 min. Synth. Commun. 2006, 36, 1795 ASYMMETRIC SYNTHESIS OF (+)‐EPI‐CYTOXAZONE G. Smitha and C. Sanjeeva Reddy Department of Chemistry, Kakatiya University, Warangal, India Synth. Commun. 2006, 36, 1801 SYNTHESIS AND SPECTRAL PROPERTIES OF MACROCYCLIC COMPOUNDS CONTAINING 1,3,4‐THIADIAZOLE MOETIES CONNECTED BY A CARBON–OXYGEN BRIDGE Anita Pati, Manabendra Patra, and Rajani K. Behera Organic Synthesis Group, Department of Chemistry, Sambalpur University, Jyoti Vihar, Burla, Orissa, India 1:1,2:2,3:3‐Macrocycles and asymmetrical macrocycles are synthesized from 2,5‐dichloro‐1,3,4‐thiadiazole and various polyethylene glycols. Synth. Commun. 2006, 36, 1809 ZINC HYDROXYAPATITE–CATALYZED EFFICIENT SYNTHESIS OF 5‐SUBSTITUTED 1H‐TETRAZOLES M. Lakshmi Kantam, V. Balasubrahmanyam, and K. B. Shiva Kumar Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, India Zinc hydroxyapatite (ZnHAP) is an effective heterogeneous catalyst for the (2+3)‐cycloaddition of sodium azide with nitriles to afford 5‐substituted 1H‐tetrazoles in good yields. The catalyst is recovered and reused for several cycles with consistent activity.

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