Graphical Abstracts

Abstract

Synth. Commun. 2005, 35, 1983

Microwave‐Assisted Dehydration and Chlorination using Phosphonium Salt

Ken‐ichi Tanji, Jiro Koshio, and Osamu Sugimoto

Laboratory of Organic Chemistry, School of Food and Nutritional Sciences, University of Shizuoka, 52‐1 Yada, Shizuoka 422‐8526, Japan

Abstract

Synth. Commun. 2005, 35, 1989

Electrochemical Oxidation of Benzylic Amines into the Corresponding Imines in the Presence of Catalytic Amounts of KI

Mitsuhiro Okimoto, Yukio Takahashi, Kaori Numata, Yuji Nagata, and Gaku Sasaki

Department of Applied and Environmental Chemistry, Kitami Institute of Technology, Koen‐cyo 165, Kitami, 090‐8507 Japan

Several benzylic amines were transformed into the corresponding imines by indirect electrooxidation using iodide ion as an electron carrier.

Abstract

Synth. Commun. 2005, 35, 1997

CuBr₂‐Catalyzed Synthesis of Bis(indolyl)methanes

Li‐Ping Mo, Zi‐Chuan Ma, and Zhan‐Hui Zhang

College of Chemistry, Hebei Normal University, Shijiazhuang, China

Copper(II) bromide is found to be an efficient catalyst for the electrophilic substitution reaction of indole with aldehydes to afford the corresponding bis(indolyl)methanes in good yields.

Abstract

Synth. Commun. 2005, 35, 2005

Improved and Highly Versatile Synthesis of 5‐Aryltropones

James Potenziano¹, Robert Spitale², and Mark E. Janik²

¹Elan Pharmaceuticals Inc., 52 Overbrook Drive, Binghamton, NY 13901, USA

²Department of Chemistry, SUNY Fredonia, Fredonia, NY 14063, USA

The use of 5‐iodo‐2‐methoxytropone in palladium(0)‐catalyzed coupling reactions with a variety of arylboronic acids has resulted in significantly improved reactions yields and times for a sterically and electronically diverse of novel A‐ring modified 5‐aryltropones.

Abstract

Synth. Commun. 2005, 35, 2017

Solvent‐Free Synthesis of Arylamides and Arylimides, Analogues of Acetylcholine

J. Trujillo‐Ferrara¹, José Correa‐Basurto¹, Judith Espinosa¹, Jazmín García¹, Francisco Martínez², and René Miranda³

¹Seccion de Estudiós del Posgrado e investigación y Departmento de Bioquímica, Escuela Superior de Medicina, Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón, México.

²Departamento de Química, Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Av. Acueducto s/n, Barrio Ticomán, México.

³Facultad de Estudios Superiores Cuautitlán, Departamento de Química, Universidad Nacional Autónoma de México, Mexico.

Various arylamides and arylimides related to acetylcholine were synthesizedunder solventless conditions. The target compounds were obtained with a good overall yield and with short reaction times.

Abstract

Synth. Commun. 2005, 35, 2025

Microwave‐Assisted Rapid Deacetalation of Carbohydrates

Mara Rubia C. Couri¹, Erúzia A. Evangelista¹, Rosemeire B. Alves¹, Maria Auxiliadora F. Prado², Rossimiriam P. F. Gil¹, Mauro V. De Almeida³, and Délio S. Raslan¹

¹Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Antônio Carlos, 6627, 31270‐901, Belo Horizonte, Brazil

²Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

³Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Juiz de Fora, Juiz de Fora, Brazil

Abstract

Synth. Commun. 2005, 35, 2033

1,4‐Conjugate Additions of Methoxyamine and 1,1‐Dimethylhydrazine to Hex‐3‐yne‐2‐one: A Facile Synthesis of Functionalized Isoxazole and Pyrazole Precursors

Ronald R. Sauers and Susan D. Van Arnum

Department of Chemistry and Chemical Biology, Wright and Rieman Laboratories, Rutgers, The State University of New Jersey, New Brunswick, New Jersey, USA

Abstract

Synth. Commun. 2005, 35, 2039

Synthesis of Symmetrical and Asymmetrical Phenethyl Thiourea Compounds as Nonnucleoside Inhibitors of HIV‐1 Reverse Transcriptase

T. K.Venkatachalam^{1, 2} and F. M. Uckun^{2, 3}

¹Department of Chemistry, Parker Hughes Institute, 2699 Patton Road, Roseville, Minnesota 55113, USA

²Drug Discovery Program, Parker Hughes Cancer Center, Roseville, Minnesota, USA

³Departments of Virology and Immunology, Parker Hughes Institute, Roseville, Minnesota, USA

Synthesis of symmetrical and asymmetrical phenethyl thioureas was accomplished in two steps with an overall yield of 75–80%. Condensation of a substitutedphenethyl amine with thiocarbonyldiimidazole, followed by treatment with one more equivalent of the phenethylamine in DMF, yielded the desired symmetrical phenethyl thiourea compound as a crystalline solid. In the case of asymmetrical thiourea derivatives, different amines were selected and condensed using a similar procedure. A series of 45 thiourea was synthesized.

Abstract

Synth. Commun. 2005, 35, 2057

Synthesis of an Oidiolactone Analogue from Abietic Acid

Paulo M. Imamura and Catarina dos Santos

Instituto de Química, Universidade Estadual de Campinas, UNICAMP C.P. 6154, 13084‐971, Campinas, São Paulo, Brazil

A synthesis of a new analogue of homosesquiterpene oidiolactone is described, starting from abietic acid.

Abstract

Synth. Commun. 2005, 35, 2067

Synthesis and Characterization of Alkyl and Aryl‐(4‐methyl‐6‐nitro‐quinolin‐2‐yl)amines: X‐Ray Structures of Ethyl and Cyclohexyl‐(4‐methyl‐6‐nitro‐quinolin‐2‐yl)amine

Melody R. Heiskell¹, Martin D. Rudd², Benjamin B. Penn³, and Jason A. Kautz⁴

¹Louisiana Scholars' College, Northwestern State University, Natchitoches, LA 71497, USA

²Department of Chemistry, University of Wisconsin—Fox Valley, Menasha, WI 54952, USA

³Institute for Non Linear Optics, NASA Marshall Space Flight Center, Huntsville, AL 35812, USA

⁴Department of Chemistry and Biochemistry, Baylor University, Waco, TX 76798 USA

A three step synthesis starting from 4‐methylquinolin‐2‐ol has led to the isolation of alkyl and aryl‐(4‐Methyl‐6‐nitro‐quinolin‐2‐yl)amines. These have been characterized by multinuclear NMR spectroscopy and the structures of two examples have been determined by a single crystal X‐ray diffraction analysis.

Abstract

Synth. Commun. 2005, 35, 2079

CONVENIENT PREPARATION OF DIETHYL (2‐THIENYL)METHANEPHOSPHONATE

Matthew C. Davis

Chemistry & Materials Division (Code 498220D), Michelson Laboratory, Naval Air Warfare Center, China Lake, CA 93555, USA.

This paper describes a convenient preparation of the phosphonate 3 in 88% overall yield.

Abstract

Synth. Commun. 2005, 35, 2085

Convenient Preparation of N,N′‐Diphenyl‐N,N′‐bis(4‐aminophenyl)‐P‐phenylenediamine

Matthew C. Davis¹, Andrew C. Chafin¹, and Aaron J. Sathrum²

¹Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USA

²Engineer and Scientist Development Program (NAWCWD), Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USA

This article describes modified conditions to prepare N,N′‐diphenyl‐N,N′‐bis(4‐aminophenyl)‐P‐phenylenediamine in 60% overall yield.

Abstract

Synth. Commun. 2005, 35, 2091

Preparation of Methyl N‐Substituted Carbamates from Amides through N‐Chloroamides

Gene A. Hiegel and Tyrone J. Hogenauer

Department of Chemistry and Biochemistry, California State University, Fullerton, California 92834, USA

Amides are chlorinated on the nitrogen using trichloroisocyanuric acid, and the N‐chloroamides are then rearranged to the corresponding methyl N‐subtituted carbamates by sodium methoxide in methanol.

Abstract

Synth. Commun. 2005, 35, 2099

Preparation of N‐Chloroamides using Trichloroisocyanuric Acid

Gene A. Hiegel, Tyrone J. Hogenauer, and Justin C. Lewis

Department of Chemistry and Biochemistry, California State University, Fullerton, California 92834, USA

Amides are efficiently converted to N‐chloroamides by trichloroisocyanuric acid (TCICA) in methanol.

Abstract

Synth. Commun. 2005, 35, 2107

Optimization of Chemo‐Enzymatic Epoxidation of Cyclohexene Mediated by Lipases

Marcelo Alves Moreira, Thiago Bergler Bitencourt, and Maria da Graça Nascimento

Departamento de Química, Universidade Federal de Santa Catarina – Florianópolis, SC, 88040‐970, Brazil

Lipases were used to generate peroxyoctanoic acid directly from octanoic acid and hydrogen peroxide and applied in situ in order to obtain cyclohexene oxide.