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Reaction Between Ethyl omega-Chloroalkylimidates and Hydrazides
It is already known that ethyl omega-chloroalkylimidate hydrochlorides and aroyl hydrazides gave, when reacted together in boiling ethanol, 2-aryl-5-omega-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-triazolo<5,1-a>pyridines were obtained from ethyl delta-chlorovalerimidate, whereas N-aroylaminoiminopyrrolidines are the products obtained from ethyl gamma-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.
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Reference£º
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem