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Abstract
Synth. Commun. 2004, 34, 961
A Novel Synthetic Approach from Diosgenin to a 17α‐Hydroxy Orthoester Via a Regio‐ and Stereo‐Specific Rearrangement of an Epoxy Ester
Nisachon Chaosuancharoen, Ngampong Kongkathip, and Boonsong Kongkathip
Natural Products and Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok, Thailand
A cholesterol model compound, containing 16β‐acetoxy, 17α‐hydroxy and (20S, 22R)‐epoxy groups, was synthesized from diosgenin in 13 steps and was rearranged regio‐ and stereo‐specifically to an orthoester with BF3·OEt2.
Abstract
Synth. Commun. 2004, 34, 985
Mono‐Nitration of Coumarins by Nitric Oxide
Liandi Lei, Desuo Yang, Zhongquan Liu, and Longmin Wu
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China
Coumarins containing a hydroxy group were nitrated by NO to afford the corresponding mono‐nitro coumarins in CH2Cl2 or CH3CN.
Abstract
Synth. Commun. 2004, 34, 993
Pinacol Coupling Reaction of Aromatic Aldehydes Mediated by Zn in Acid Aqueous Media Under Ultrasound Irradiation
Jin‐Hui Yang, Ji‐Tai Li, Jun‐Ling Zhao, and Tong‐Shuang Li
College of Chemistry and Environmental Science, Hebei University, Hebei Province, Baoding, P.R. China
Pinacol coupling of aromatic aldehydes by Zn powder in aqueous H2NSO3H or H3PO4 under ultrasound irradiation can lead to the corresponding pinacols in 14–88% yields.
Abstract
Synth. Commun. 2004, 34, 1001
Synthesis of all Stereoisomers of the Norchrysanthemic Acid Methyl Ester
Kazuya Ujihara,1 Noritada Matsuo,1 and Takeshi Kitahara2
1Agricultural Chemicals Research Laboratory, Sumitomo Chemical Co., Ltd., Takarazuka, Hyogo, Japan
2Department of Applied Biology, Graduate School of Agricultural and Biological Sciences, The University of Tokyo, Tokyo, Japan
Syntheses of eight stereoisomers of methyl norchrysanthemate, (1R)‐trans‐(Z)‐isomer and (1R)‐trans‐(E)‐isomer from (1R)‐trans‐chrysanthemic acid, and other six isomers from (+)‐3‐carene, are described.
Abstract
Synth. Commun. 2004, 34, 1011
A Convenient Selenium‐Linking Strategy for Traceless Solid‐Phase Synthesis of Diethyl 1‐Alkenephosphonates
Shou‐Ri Sheng, Wei Zhou, Xiao‐Ling Liu, and Cai‐Sheng Song
Department of Chemistry, Jiangxi Normal University, Nanchang, P.R. China
A novel polymer‐supported α‐diethoxyphosphoryl methyl selenide has been developed and applied to convenient preparation of diethyl trans‐1‐alkenephosphonates in good yields and purities.
Abstract
Synth. Commun. 2004, 34, 1017
An Efficient Method for Synthesis of 4‐(Phosphonomethyl)Benzene Derivatives Under Solvent‐Free Conditions
Ting Yang, Changxue Lin, Hua Fu, Yuyang Jiang, and Yufen Zhao
Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing, P.R. China
A simple, efficient and general method has been developed for synthesis of 4‐(phosphonomethyl)benzene derivatives through one‐pot reaction of phosphoric acid, 4‐substitute benzyl chlorides and hexamethyldisilazane under solvent‐free conditions and the following hydrolysis in 2M NH3·H2O
Abstract
Synth. Commun. 2004, 34, 1023
Reagent‐Controlled Asymmetric Iodolactonization using Cinchona Alkaloids as Chiral Sources
Mang Wang, Lian Xun Gao, Wei Yue, and Wen Peng Mai
Lab 2, Changchun Institute of Applied Chemistry, Chinese Academy of Science, Changchun, P.R. China
A novel method for reagent‐controlled asymmetric iodolactonization of 5‐anyl‐4‐pentenoic acids is reported. This work uses carboxylate ion pairs combined with cinchona alkaloids as chiral sources of carboxylate anion for the first time leading to a mixture of two regio‐isomeric iodolactones with moderate enantioselectivity (exo‐18.5% ee, endo‐35.0% ee) under mild reaction conditions.
Abstract
Synth. Commun. 2004, 34, 1033
Efficient Synthesis of 2,8‐Diphosphatricyclo[5.3.1.12,6]dodeca‐3,5,9‐triene 2,8‐Dioxides
J. Kovács,1 T. Imre,2 K. Ludányi,2 L. Toke,3 and G. Keglevich1
1Department of Organic Chemical Technology, Budapest University of Technology and Economics, Budapest, Hungary
2Hungarian Academy of Sciences, Chemical Research Center, Budapest, Hungary
3Research Group of the Hungarian Academy of Sciences at the Department of Organic Chemical Technology, Budapest University of Technology and Economics, Budapest, Hungary
Depending on the P‐substituent, the reaction of dihydrophosphinine oxides with TCNE may give two kinds of products.
Abstract
Synth. Commun. 2004, 34, 1041
Synthesis of ortho‐Methoxyphenylsulfonylsemicarbazides
N. Lebegue, G. Bethegnies, and P. Berthelot
Laboratoire de Chimie Thérapeutique, Faculté des Sciences Pharmaceutiques et Biologiques de Lille, Lille Cedex, France
Abstract
Synth. Commun. 2004, 34, 1049
An Improved Preparation of N 2‐tert‐Butoxycarbonyl‐ and N 2‐Benzyloxycarbonyl‐(S)‐2,4‐Diaminobutanoic Acids
Ryszard Andruszkiewicz and Dorota Rożkiewicz
Department of Pharmaceutical Technology and Biochemistry, Gdańsk University of Technology, Gdańsk, Poland
An improved synthetic route to selectively protected (S)‐2,4‐diamnobutanoic acids is described.
Abstract
Synth. Commun. 2004, 34, 1057
Directing Effect of Axial and Equatorial Anomeric Substituent in Site Specific Glycosylation of Glucopyranosides
Hari Babu Mereyala, S. Bhavani, and A. P. Rudradas
Organic Chemistry Division III, Indian Institute of Chemical Technology, Hyderabad, India
Abstract
Synth. Commun. 2004, 34, 1065
Mukaiyama Aldol Reactions of Silyl Enolates Catalyzed by Iodine
Prodeep Phukan
Department of Chemistry, Gauhati University, Guwahati, India
Iodine has been found to catalyze Mukaiyama aldol reaction of silyl enolates with aldehydes, ketones and acetals in good yield.
Abstract
Synth. Commun. 2004, 34, 1071
Efficient DMTMM Promoted Nucleoside Loading of CPG Solid Support for Oligonucleotide Synthesis
Matthew C. Uzagare,1 Yogesh S. Sanghvi,2,3 and M. M. Salunkhe1
1Department of Chemistry, The Institute of Science, Mumbai, India
2Development Chemistry, Isis Pharmaceuticals, Inc., Carlsbad, California, USA
3Raisayan Inc., Encinitas, California, USA
A simple and efficient process for the attachment of protected 2′‐deoxynucleosides to the solid support CPG via succinyl linkage using the mild, non‐carbodiimide dehydrating agent 4‐(4,6‐dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methylmorpholinium chloride (DMTMM) has been developed.
Abstract
Synth. Commun. 2004, 34, 1079
Nitric acid mediated oxidative transformation of thiols to disulfides
Anup Kumar Misra and Geetanjali Agnihotri
Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India
Oxidation of thiols to disulfides are reported using nitric acid/methylene chloride.
Abstract
Synth. Commun. 2004, 34, 1087
A Facile Reduction Procedure for N,N′‐bis[5‐substituted salicylidene]‐m/p‐phenylenediamines with Sodium Borohydride–Silica Gel System
V. Sridharan, S. Muthusubramanian, and S. Sivasubramanian
Department of Organic Chemistry, Madurai Kamaraj University, Madurai, India
Abstract
Synth. Commun. 2004, 34, 1097
Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene
P. Narendar, B. Gangadasu, Ch. Ramesh, B. China Raju, and V. Jayathirtha Rao
Organic Chemistry Division II, Indian Institute of Chemical Technology, Hyderabad, India
Chloromethylpyridines and chloropyridines were prepared by using diphosgene and triphosgene as chlorinating agents.
Abstract
Synth. Commun. 2004, 34, 1105
A Convenient Synthesis of Novel 1‐[2‐(Benzimidazol‐2‐yl)ethoxy]‐2,6‐Diarylpiperidin‐4‐ones
C. Ramalingan, S. Balasubramanian, and S. Kabilan
Department of Chemistry, Annamalai University, Annamalainagar, India
2,6‐Diarylpiperidin‐4‐ones upon strategical N‐hydroxylation, cyanoethylation followed by acid aided condensation with o‐phenylenediamine afforded a convenient route to novel 1‐[2‐benzimidazol‐2‐yl)ethoxy]‐2,6‐diarylpiperidin‐4‐ones.
Abstract
Synth. Commun. 2004, 34, 1117
Synthesis of β‐keto Esters Promoted by Yttria‐Zirconia Based Lewis Acid Catalyst
Rajesh K. Pandey, Anis N. Deshmukh, and Pradeep Kumar
Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune, India
A variety of aldehydes react with diazoacetates in the presence of yttria‐zirconia based catalyst to afford the corresponding β‐keto esters in excellent yields.
Abstract
Synth. Commun. 2004, 34, 1125
Synthesis of a Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella Dysenteriae Type 9 in the form of its 2‐(Trimethylsilyl)ethyl Glycoside
Samarpita Roy, Sujit Kumar Sarkar, and Nirmolendu Roy
Department of Biological Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, India
Abstract
Synth. Commun. 2004, 34, 1141
Microwave Assisted Synthesis of Fluorinated Hexahydro 1,3,5‐Triazine Derivatives in Aqueous Medium and One Pot Synthesis of 1,2,4‐Triazolo(4,3‐a)1,3,5‐triazines
Anshu Dandia, Kapil Arya, and Meha Sati
Department of Chemistry, University of Rajasthan, Jaipur, India
Triazolo[4,3‐a]triazines are synthesized by a one‐pot reaction of ‘in situ’ synthesized triazinyl hydrazine with CS2 under microwave irradiation is described.
Abstract
Synth. Commun. 2004, 34, 1157
A Facile Synthesis of Novel [4‐(Aryl)‐3a,4,5,9b‐TetrahydroCyclopenta [c]Quinolin‐8‐Ylmethyl]‐8′‐(4′‐Aryl)‐3a′,4′,5′, 9b′‐Tetrahydro‐3H‐Cyclopenta[c]Quinolines: Indium Trichloride Catalyzed Intermolecular Imino Diels–Alder Reaction of Cyclopentadiene with Schiff'S Bases
S. Nandagopal, B. Geetha, and P. T. Perumal
Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai, India
Abstract
Synth. Commun. 2004, 34, 1163
The Reaction of Hydrazine with α‐Cyanocinnamate Esters: a Caveat
Paul J. Erdman, Jimmy L. Gosse, Jamey A. Jacobson, and David E. Lewis
Department of Chemistry, University of Wisconsin—Eau Claire, Eau Claire, Wisconsin, USA
α‐Cyanocinnamate esters react with hydrazine to give initial products of conjugate addition that then undergo a fragmentation to give the azine of the carbonyl precursor to the starting ester, rather than intramolecular aminolysis to give the pyrazolidinone.
