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Problems related to the synthesis of 3‐aziridinyl‐6‐chloropyridazine
Author(s) -
Nyberg Wayne H.,
Cheng C. C.
Publication year - 1964
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.5570010101
Subject(s) - chemistry , pyridazine , ring (chemistry) , nucleophile , pyrimidine , group (periodic table) , medicinal chemistry , displacement (psychology) , nucleophilic substitution , stereochemistry , organic chemistry , catalysis , psychology , psychotherapist
The correct structure of the reported 3‐aziridinyl‐6‐chloropyridazine was found to be 3‐[β‐(1‐aziridinyl)ethylamino]‐6‐chloropyridazine, which was confirmed by n. m. r. studies. The relative ease of nucleophilic displacement of a methylsulfonyl group versus a chloro group in equivalent positions on a pyridazine or a pyrimidine ring was compared. It was observed that the chloro rather than the methylsulfonyl group was preferentially replaced, as illustrated by substitution studies of 3‐chloro‐6‐methylsulfonylpyridazine and 4‐chloro‐6‐methylsulfonylpyrimidine.