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Reactions of 2‐amino‐, 2‐alkylamino‐, and 2‐piperidino‐1‐azaazulenes with aryl and chlorosulfonyl isocyanates
Author(s) -
Abe Noritaka,
Matsuda Haruhiko,
Sugihara Yoshikazu,
Kakehi Akikazu
Publication year - 1996
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.5570330453
Subject(s) - chemistry , isocyanate , aryl , azulene , medicinal chemistry , phenyl isocyanate , organic chemistry , polyurethane , alkyl
Reaction of 2‐amino‐1‐azaazulene with phenyl isocyanate gave 3‐phenyl‐2 H ‐3,4‐dihydro‐1,3,4a‐triazabenz[5,4‐ a ]azulene‐2,4‐dione. Reactions of 2‐alkylamino‐1‐azaazulenes with aryl isocyanates gave 2‐( N ‐ethyl‐ N ′‐arylureido)‐1‐azaazulenes initially, which rearranged to N ‐aryl‐2‐alkylamino‐1‐azaazulene‐3‐carboxamides and successive reaction with another molar amount of aryl isocyanate furnished uracil‐fuzed 1‐azaazulenes. Reaction of 2‐piperidino‐1‐azaazulene with aryl isocyanate gave N ‐aryl‐2‐piperidino‐1‐azaazulene‐3‐carboxamide. Reaction of 2‐(substituted amino)‐1‐azaazulenes with chlorosulfonyl isocyanate gave 3‐cyano‐ and 3‐chloro‐2‐(substituted amino)‐1‐azaazulenes.