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

Konstantin G. Nazarenko; Nataliya A. Shtil; Alexander N. Chernega; Miron O. Lozinskii; Andrey A. Tolmachev

doi:10.1055/s-2004-822375

PAPER

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

Konstantin G. Nazarenko*^a, Nataliya A. Shtil^b, Alexander N. Chernega^a, Miron O. Lozinskii^a, Andrey A. Tolmachev^c
^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

Abstract

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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

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References

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