F. Kóródi
1996
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Journal
Heterocyclic Communications
Abstract
Synthesis of 2-(1H-1,2,4-triazol-1-yl)quinolines by the reaction of 2-chloroquinolines with 1,2,4-triazole was studied under neutral, acidic and basic reaction conditions. Significant role of the acid and base catalysis as well as substituent effects on the reactivity of 2-chloroquinolines in these reactions are reported. As a result of this study one can choose the best reaction conditions for the preparation of the title compounds according to the substituents on the quinoline ring. INTRODUCTION In the first paper of this series (1) a brief summary of the background and aim of our study has been given and the results related to the 4-chlorquinolines have been reported. In this paperthe results concerning the nucleophilic substitution reaction of 2-chloroquinolines with 1,2,4-triazole are reported. RESULTS AND DISCUSSION There are some well known differences in behaviour of 2-chloroand 4-chloroquinoline in nucleophilic substitution reactions. The two major ones are that 2-chloroquinoline has less tendency to show acid catalytic or autocatalytic effect when treated with amines (2,3), but shows higher reactivity toward methoxide ions (2) than 4-chloroquinoline.The same general methods were used as in our previous work (1) in order to establish the main characteristic features of the reaction of 2-chloroquinolines with 1,2,4-triazole, and to reveal similarities and differences between 4-chloroand 2-chloro-quinolines in this reaction with special regard to the role of acid and base catalysis and effect of the substituents on the reactivity. Accordingly, 2-chloroquinolines were reacted with 1,2,4-triazole (method A), or with 1,2,4-triazole in the presence of hydrochloric acid (method B), or with sodium salt of 1,2,4-triazole (method C).