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Synthesis 2010(2): 288-292  
DOI: 10.1055/s-0029-1217100
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Synthesis of New Types of Benzodiazepine Derivatives: 2-Alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepin-4-ones and 2-Alkyl­sulfanyl-3H-4,5-dihydro-1,3-benzodiazepine-4-thiones

Shuhei Fukamachi, Akihiro Kobayashi, Hisatoshi Konishi, Kazuhiro Kobayashi*
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 26 August 2009
Publication Date:
03 November 2009 (online)

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Abstract

An efficient method for preparing 2-alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepin-4-ones and 2-alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepine-4-thiones under mild conditions has been developed. Thus, 2-(2-isocyanophenyl)acetamides and 2-(2-isocyanophenyl)thioacetamides, easily available from respective 1-isocyano-2-methylbenzenes, were converted into the corresponding isothiocyanates on treatment with sulfur in the presence of a catalytic amount of selenium, which were then reacted with an equimolar amount to sodium hydride to give 2-(sodiosulfanyl)-3H-4,5-dihydro-1,3-benzodiazepin-4-one and 2-(sodiosulfanyl)-3H-4,5-dihydro-1,3-benzodiazepine-4-thione intermediates, respectively. These intermediates were allowed to react with various alkyl halides to afford the desired benzodiazepinone or benzodiazepinethione derivatives in a one-pot reaction.

Key words

benzodiazepines - isocyanides - isothiocyanates - sulfur - cyclization

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