HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Special Issue
Victor Snieckus's Special Issues, Vol. 88, No. 2, 2014
Published online: 27th September, 2013
■ Palladium-Catalyzed Cross-Coupling Reaction of Trialkylbismuthines with 2-Haloazines and Diazines
Pauline Petiot and Alexandre Gagnon*
*Département de chimie, UQAM - Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada
Abstract
An efficient method for the cross-coupling reaction of primary trialkybismuth reagents with 2-haloazines and diazines is reported. The reaction functions with pyridines, pyrimidines, pyridazines and pyrazines and tolerates many functional groups. This method gives access to 2-alkylazines and diazines, a class of compounds which is important in medicinal chemistry.
Published online: 8th November, 2013
■ Acid-Promoted Aromatization of Perylene-Based Endoxides
Alejandro Criado, Manuel Vilas-Varela, Agustín Cobas, Dolores Pérez, Diego Peña, and Enrique Guitián*
*Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, E-15706 Santiago de Compostela, Spain
Abstract
The aromatization of perylene-based endoxides by treatment with HCl and EtOH has been studied.
Published online: 7th November, 2013
■ Synthesis and Properties of Conducting Polymer Nanotubes with Redox-Active Tetrathiafulvalene
Shinya Nambu, Tsukasa Nakahodo, and Hisashi Fujihara*
*Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan
Abstract
Electropolymerization of a new chiral (S)-binaphthyltetrathiafulvalenyl-terthiophene, 1-TTF, produced the corresponding polymer films on an electrode surface. The polymer nanotubes consisting of the tetrathiafulvalene and polythiophene were synthesized from the template-based electropolymerization of 1-TTF in a nanoporous alumina template.
Published online: 26th November, 2013
■ Regio- and Enantioselective Nitrone Cycloaddition to Alkynones for the Synthesis of Δ4-Isoxazolines
Mukund P. Sibi,* Kelsey L. Dunkle, and Digamber Rane
*Department of Chemistry and Biochemistry, North Dakota State University, Fargo, North Dakota 58108, U.S.A.
Abstract
We report herein a strategy for Lewis acid catalyzed enantioselective 1,3-dipolar cycloaddition of nitrones with alkynones to generate Δ4-isoxazolines. The corresponding cycloadducts were isolated as a single regioisomer with high yields and enantioselectivities.
Published online: 20th November, 2013
■ A Formal PCB-Free Synthesis of (-)-GSK1360707 via a Double Alkylation Reaction
Vassil I. Elitzin, Matthew J. Sharp, and Elie A. Tabet*
*Product Development, GlaxoSmithKline, Research Triangle Park, North Carolina 27709, U.S.A.
Abstract
The formal synthesis of the triple reuptake inhibitor (-)-GSK1360707 is described. The synthesis features an intramolecular cyclization and a double alkylation sequence to produce the 3-azabicyclo[4.1.0]heptane skeleton. An advantage of this route is the absence of PCB generation which plagued an earlier route.
Published online: 8th November, 2013
■ Improved Synthesis of Antipsychotic Drug Bifeprunox
Gerhard Laus, Sven Nerdinger,* Volker Kahlenberg, and Herwig Schottenberger
*Sandoz GmbH, Biochemiestrasse 10, 6250 Kundl , Austria
Abstract
A new and efficient six-step synthesis of the antipsychotic drug bifeprunox is reported. The key step is azidation of a lithiated phenol ether. Subsequent reduction of the azide, removal of phenol protecting group, and cyclization lead to the desired benzoxazolinone.
Published online: 15th November, 2013
■ Asymmetric Alkylation of α-Cyanosulfones Catalyzed by Chiral 1,2,3-Triazolium Salts
Kohsuke Ohmatsu, Yusuke Hakamata, Ayano Goto, and Takashi Ooi*
*Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan
Abstract
Chiral 1,2,3-triazolium salt-catalyzed asymmetric phase-transfer alkylation of α-cyanosulfones has been developed. This protocol is applicable to a variety of benzylic and allylic halides and cyanosulfones, affording chiral sulfones possessing tetrasubstituted carbons in excellent yields with good-to-high enantioselectivities.