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A new route to functionalized 3-aminopyridazines by ANRORC type ring transformation of 1,2,4-triazines with carbon nucleophiles

✍ Scribed by Andrzej Rykowski; Ewa Wolinska; Henk C. Van Der Plas

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
314 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of 3‐chloro‐6‐phenyl‐1,2,4‐triazine 1a with carbon nucleophiles 2ad bearing a cyano substituent at a carbanionic center has been studied. In all reactions the formation of the corresponding 3‐aminopyridazines 3ad takes place via ANRORC mechanism involving addition of the nucleophile at position 5 in compound 1a, ring opening with breaking of the N~4~C~5~ bond and intramolecular ring closure of the resulting open‐chain intermediate. A ^15^N study with labeled phenylacetonitrile 2a* has shown that the nitrogen atom of the exocyclic amino group of 3‐amino‐4,6‐diphenylpyridazine 3a was originally present in phenylacetonitrile.

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