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Abstract
Graphical Abstract Section
Abstract
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
Abstract
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.
Abstract
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.
Abstract
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.
Abstract
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%.
Abstract
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:
Abstract
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.
Abstract
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.
Abstract
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.
Abstract
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
Abstract
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
Abstract
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
Abstract
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.
Abstract
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.
Abstract
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.
Abstract
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.
Abstract
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.
Abstract
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.
Abstract
Synth. Commun. 2006, 36, 1795
ASYMMETRIC SYNTHESIS OF (+)‐EPI‐CYTOXAZONE
G. Smitha and C. Sanjeeva Reddy
Department of Chemistry, Kakatiya University, Warangal, India
Abstract
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.
Abstract
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.
