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Nucleophilic substitution of 1,2,4‐triazines
Author(s) -
Huang Jim J.
Publication year - 1985
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.5570220537
Subject(s) - chemistry , nucleophilic substitution , yield (engineering) , triazine , methanethiol , nucleophile , ammonia , medicinal chemistry , substitution reaction , substitution (logic) , organic chemistry , sulfur , catalysis , materials science , computer science , metallurgy , programming language
The reaction of 3‐(methylthio)‐5‐carbethoxy‐1,2,4‐triazine (5) with ammonia was found to yield products from not only ammonia but also methanethiolate displacements. An account of the transformations and the products observed is given. The 3‐position of 3,6‐bis(methylthio)‐5‐carbamoyl‐1,2,4‐triazine (7) was shown to be more reactive than the 6‐position toward nucleophilic substitution. Reduction at the 4,5 positions of triazine 5 occurred upon treatment with methanethiol under basic and neutral conditions.