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Synthesis 2009(24): 4113-4118  
DOI: 10.1055/s-0029-1217079
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Novel N-Thiazolo-1,3-oxathiol-2-imines from α-Haloketones Using Potassium Thiocyanate-Silica Gel

Tadashi Aoyama*a, Izumi Araia, Takuo Matsumotob, Toshio Takidoa, Mitsuo Kodomaric
a Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
b Biologics Research Laboratories, Daiichi Sankyo Co., Ltd., 1-16-13 Kitakasai Edogawa-ku, Tokyo 140-8710, Japan
c Department of Bioscience and Engineering, Shibaura Institute of Technology, Fukasaku, Minuma-ku, Saitama 337-8570, Japan
Fax: +81(3)32590818; e-Mail: aoyama@chem.cst.nihon-u.ac.jp;
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Publication History

Received 21 July 2009
Publication Date:
26 October 2009 (online)

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Abstract

Novel N-thiazolo-1,3-oxathiol-2-imines are synthesized by reaction of α-haloketones with potassium thiocyanate-silica gel. It is thought that the reaction occurs through conversion of the α-haloketone into the corresponding thiocyanate which then undergoes acid-catalyzed intramolecular cyclization to yield a cationic intermediate. Subsequent reaction of this intermediate with another molecule of the α-thiocyanatoketone and a second cyclization then gives the N-thiazolo-1,3-oxathiol-2-imine.

Key words

N-thiazolo-1,3-oxathiol-2-imines - potassium thiocyanate-silica gel - heterocycles

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