Chemistry of Heterocyclic Compounds p. 414 - 420 (1989)
Update date:2022-08-03
Topics:
Attaryan, O. S.
Asratyan, G. V.
Eliazyan, G. A.
Panosyan, G. A.
Kinoyan, F. S.
Darbinyan, E. G.
The phase-transfer catalyzed (PTC) alkylation of pyrazoles and 1,2,4-triazole with cis- and trans-1,4-dichloro-2-butenes (DCB) has been examined.The monoalkylation products of pyrazoles with cis-DCB are bicyclic salts formed by intramolecular cyclization of the intermediate cis-1-(4-chloro-2-butenyl)pyrazoles.The corresponding trans-compounds are incapable of cyclization, but on prolonged standing they undergo intermolecular polyquaternization.Both cis- and trans-DCB undergo phase-transfer catalyzed reaction with 1,2,4-triazole to give polymeric quaternary salts.Conditions have been worked out for the dehydrochlorination of 1-(4-chloro-2-butenyl)azoles to 1-(butadien-2-yl)azoles.
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