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Synthesis 2004(8): 1195-1202  
DOI: 10.1055/s-2004-822375
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© Georg Thieme Verlag Stuttgart · New York

2-Hetaryl Derivatives of 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine

Konstantin G. Nazarenko*a, Nataliya A. Shtilb, Alexander N. Chernegaa, Miron O. Lozinskiia, Andrey A. Tolmachevc
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya 5, Kyiv-94, 02094, Ukraine
b Chernigov State University of Technology, Shevchenko 95, Chernigov, 14027, Ukraine
Fax: +38(44)5590480; e-Mail: Shnataliya@ukr.net;
c Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
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Publication History

Received 12 February 2004
Publication Date:
10 May 2004 (online)

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Abstract

A new approach for the synthesis of 2-hetaryl derivatives of 3-oxo-3,4-dihydro-2H-1,4-benzothiazines is described. 2-Chloro derivatives of 2a,b were reacted with electron-rich heterocycles 3-14 under basic catalysis (with a slight excess of Et3N) to provide the substitution products 16-36. In the reaction of 2b with 14 and 15, an intermolecular cyclization took place between the amino and ethoxycarbonyl groups, resulting in spiro compounds 35 and 36, respectively.

Key words

chloro derivatives - electron-rich heterocycles - electrophilic substitution - cyclization - spiro compounds