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Reaction Between Ethyl ω-Chloroalkylimidates and Hydrazides
Bonanomi, Michele,Baiocchi, Leandro
, p. 1657 - 1660 (2007/10/02)
It is already known that ethyl ω-chloroalkylimidate hydrochlorides and aroyl hydrazides gave, when reacted together in boiling ethanol, 2-aryl-5-ω-haloalkyl-1,3,4-oxadiazoles.It has now been found that the reaction follows a different course in the presence of triethylamine.In particular, 2-aryl-5,6,7,8-tetrahydro-1,2,4-triazolopyridines were obtained from ethyl δ-chlorovalerimidate, whereas N-aroylaminoiminopyrrolidines are the products obtained from ethyl γ-chlorobutyrimidate.A similar case, in which the closure of the triazole ring to obtain a dihydropyrrolotriazole was found to be more difficult than the corresponding closure to a tetrahydrotriazolopyridine, is described.Also the reaction between the imidates and carbethoxyhydrazine, which gives piperidine and pyrrolidine derivatives, is reported.
