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A new route to functionalized 3‐aminopyridazines by ANRORC type ring transformation of 1,2,4‐triazines with carbon nucleophiles
Author(s) -
Rykowski Andrzej,
Wolinska Ewa,
Van Der Plas Henk C.
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370434
Subject(s) - chemistry , nucleophile , ring (chemistry) , substituent , intramolecular force , nitrogen atom , triazine , carbon atom , stereochemistry , intramolecular reaction , carbon fibers , medicinal chemistry , organic chemistry , catalysis , materials science , composite number , composite material
The reaction of 3‐chloro‐6‐phenyl‐1,2,4‐triazine 1a with carbon nucleophiles 2ad bearing a cyano substituent at a carbanionic center has been studied. In all reactions the formation of the corresponding 3‐aminopyridazines 3ad 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.