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Reaction of tetraazathiapentalene and thiadiazolopyrimidine derivatives with heterocumulenes: Cycloaddition and elimination reactions via hypervalent sulfur intermediates
Author(s) -
Matsumura Noboru,
Ito Atsushi,
Tomura Masaaki,
Okumura Yasuyuki,
Mizuno Kazuhiko
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410116
Subject(s) - chemistry , hypervalent molecule , cycloaddition , reactivity (psychology) , sulfur , carbon disulfide , phenyl isothiocyanate , thermal decomposition , isothiocyanate , medicinal chemistry , derivative (finance) , elimination reaction , organic chemistry , catalysis , reagent , medicine , alternative medicine , pathology , financial economics , economics
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.