Ring transformations in reactions of heterocyclic halogeno compounds with nucleophiles (XXVIII) A study of the mechanism of transformation of chloropyrazine into 2‐cyanoimidazole using 14C‐ and 15N‐labelling
- 1 January 1973
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 92 (3) , 311-316
- https://doi.org/10.1002/recl.19730920311
Abstract
The mechanism of the conversion of chloropyrazine into 2‐cyanoimidazole by the action of potassium amide in liquid ammonia has been investigated. Using 2‐chloro[4′ 15N]pyrazine and 2‐chloro[2′ 14C]pyrazine it has been shown that ring contraction occurs by a nucleophilic attack of the amide ion at C(3), followed by fission of the C(3)‐N(4) bond.Keywords
This publication has 3 references indexed in Scilit:
- Ring transformations in reactions of heterocyclic halogeno compounds with nucleophiles (XXV): On the mechanism of the conversion of chloropyrazine into aminopyrazine and of 2‐chloroquinoxaline into 2‐aminoquinoxaline with potassium amide in liquid ammoniaRecueil des Travaux Chimiques des Pays-Bas, 1972
- Ring transformations in reactions of heterocyclic halogeno compounds with nucleophtiles (XXIV): Study of the mechanisms of the conversion of 2‐halogenoquinoxalines into 2‐aminoquinoxalines and benzimidazole by potassium amide in liquid ammoniaRecueil des Travaux Chimiques des Pays-Bas, 1972
- Ring transformations in reactions of heterocyclic halogeno compounds with nucleophiles (XXI): Conversion of 2‐chloropyrazine into imidazole and 2‐cyanoimidazole by potassium amide in liquid ammoniaRecueil des Travaux Chimiques des Pays-Bas, 1971