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Isothiazoles. III. Synthesis of isothiazolo [5,4‐ d ] pyrimidines
Author(s) -
Anderson Richard C.,
Hsiao Y. Y.
Publication year - 1975
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.5570120514
Subject(s) - chemistry , xanthate , hydrolysis , amide , medicinal chemistry , primary (astronomy) , organic chemistry , stereochemistry , physics , astronomy
5‐Amino‐3‐methylisothiazole‐4‐carbonitrile 2 was prepared by oxidation of 3‐amino‐2‐cyano‐thiocrotonamide 1 . A series of 4‐amino‐3‐methylisothiazolo[5,4‐ d ]pyrimidines 6 was derived from 2 by reaction with orthoesters followed by cyclization with primary amines. Hydrolysis of 2 to the corresponding amide 10 followed by cyclization with orthoesters gave the corresponding 5 H ‐isothiazolo[5,4‐ d ]pyrimidin‐4‐ones 11 . Reactions of 2 and 10 with sodium methyl xanthate gave the corresponding pyrimidinethione derivatives 12 and 13.