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Synthesis 2010(15): 2588-2598  
DOI: 10.1055/s-0029-1218840
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Synthesis of Annulated Thiatriazine Dioxides

Alexander N. Khodachenkoa,b, Alexander N. Shivanyuk*a,c, Svetlana V. Shishkinad, Oleg V. Shishkind, Konstantin G. Nazarenkoe, Andrey A. Tolmacheva,f
a ChemBioCenter, Taras Shevchenko Kiev National University, 62 Volodymyrska St., Kiev 01033, Ukraine
b Taras Shevchenko Chernigiv State Pedagogical University, 53 Getman Polubotok St., Chernigiv 14013, Ukraine
c The Institute of High Technologies, Taras Shevchenko Kiev National University, 62 Volodymyrska St., Kiev 01033, Ukraine
d STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, 60 Lenina Ave., Kharkiv 61001, Ukraine
e Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kiev 02094, Ukraine
f Enamine Ltd., 23 Alexander Matrosov St., Kiev 01103, Ukraine
Fax: +380(44)5373253; e-Mail: shivan1@yandex.ru;
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Publication History

Received 1 March 2010
Publication Date:
25 June 2010 (online)

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Abstract

The reactions of five-, six-, seven-, and eight-membered cyclic imido ethers with one equivalent of sulfamide lead to the corresponding sulfamoylamidines in 70-80% yields. Sulfamoyl­amidines undergo condensations with aliphatic and aromatic aldehydes as well as aliphatic ketones to give thiatriazine dioxides in 50-95% yields. The NMR spectroscopic studies reveal ring-chain tautomerism of some thiatriazine dioxides in solution. The ratio between the tautomers depends on the temperature, solvent polarity, and electronic properties of the substituents of the pendant aryl rings. Thiatriazine dioxides are readily alkylated and acylated at position 2.

Key words

imido ethers - sulfamide - sulfamoylamidines - thiatria­zine dioxides - tautomerism

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