Reactions of 3-phenyl-8-triphenylphosphoimino-1-azaazulene with aryl isocyanate, aryl isothiocyanate, and carbon disulfide

Creators Nagamatsu Kentaro

Creators Fujii Hiroyuki

Creators Abe Noritaka

Creators Kakehi Akikazu

Reaction of 3-phenyl-8-triphenylphosphoimino-1-azaazulene (1) with some aryl isocyanates gave 2-arylimino-4-phenyl-2,2a-dihydro-1,2a-diazacyclopent[cd]azulenes (2) and 8-arylimino-1,8-dihydro-1-azaazulenes (3). Reaction of 1 with p-toluenesulfonyl isocyanate gave 2-imino-3-(p-methylphenyl)-4-phenyl-2,2a-dihydro-1,2a-diazacyclopent[cd]azulene as cyclization-rearrangement product. Reaction of phenyl isothiocyanate gave 2. Tautomerization of between 8-imino-1,8-dihydro-1-azaazulenes (3) and 8-amino-1-azaazulenes was discussed on the basis of X-Ray structure analysis and molecular orbital calculation.

[ISSN]0385-5414

[NCID]AA00663739