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Synthesis and Some Reactions of 2-Amino-1-azaazulene-3-carbaldehyde
Abe, Noritaka,Tanaka, Keiko,Yamagata, Satoshi,Satoh, Akira,Yamane, Kameji
, p. 340 - 344 (1992)
2-Chloro-1-azaazulene-3-carbaldehyde (1a) reacted with pyridine, followed by a reaction with piperidine to give 2-amino-1-azaazulene-3-carbaldehyde (1b) in excellent yield.Compound 1b was also obtained by a Vilsmeier-Haack reaction of 2-amino-1-azaazulene.Acetylation of 1b yielded a 2-acetylamino derivative, whereas methylation gave a 1-methylated compound.Reactions of 1b with hydrazines and alkylamines gave the corresponding hydrazones and Schiff bases, respectively, in excellent yields.The reactions of 1b with active methylene compounds gave 1,10-diazabenzazulen-2(1H)-one derivatives.The reaction of 1b with guanidine gave pyrimidine-fuzed 1-azaazulene.
