Reactions of 2-hydrazino-1-azaazulenes with diphenylcyclopropenone

Creators Abe Noritaka

Creators Kakehi Akikazu

The reaction of ethyl 2-hydrazino-1-azaazulene-3-carboxylate with diphenylcyclopropenone (DPP) gave ethyl (Z)-2-[N'-(3-amino-2,3-diphenylpropenoyl)hydrazino]-1-azaazulene-3-carboxylate, ethyl 8,9-diphenyl-1,2,9b-triazaindeno[1,7,6-bcd]azulene-3-carboxylate, ethyl (E)-3-(1,2-diphenylethyl)-1,2,3a-triazacyclopent[a]azulene-9-carboxylate, and ethyl 2-amino-1-azaazulene-3-carboxylate (8a), together with the products of 8a with DPP. However, the reaction of 2-hydrazino-1-azaazulene with DPP gave 4H-2,3-diphenyl-1,4a-diazabenz[a]azulen-4-one, (Z)-3-[(1-azaazulen-2-yl)amino]-2,3-diphenylpropenamide, 3,4-diphenyl-3,4-dihydro-2H-1,4a-diazabenz[a]azulen-2-one and 2-amino-1-azaazulene. The structures of the obtained products were determined by inspections of their physical and spectral data, as well as single-crystal X-ray structure analyses of some of these compounds. The reaction mechanisms are discussed.

[ISSN]0009-2673

[NCID]AA00580132

https://doi.org/10.1246/bcsj.67.2487

[isPartOf] [URI]http://www.jstage.jst.go.jp/browse/bcsj/-char/en