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Reaction of tetraazathiapentalene and thiadiazolopyrimidine derivatives with heterocumulenes: Cycloaddition and elimination reactions via hypervalent sulfur intermediates

✍ Scribed by Noboru Matsumura; Atsushi Ito; Masaaki Tomura; Yasuyuki Okumura; Kazuhiko Mizuno

Publisher: Journal of Heterocyclic Chemistry
Year: 2004
Tongue: English
Weight: 147 KB
Volume: 41
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570410116

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✦ Synopsis

Abstract

Tetraazathiapentalene derivative 1 reacts with heterocumulenes such as diphenylketene (2) and 2‐pyridylisothiocyanate (5) to give heterocycles 3, 6 and 7 with elimination of methylisothiocyanate. The reactions of thiadiazolopyrimidine derivatives 8a‐b with ethoxycarbonyl isothiocyanate (9) and carbon disulfide (11) gives heterocycles 10 and 12 via thermal decomposition of 1:1 cycloadducts C and D which have a hypervalent sulfur. The mechanistic and reactivity features of these reactions are described.

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