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Pyrimidine derivatives and related compounds. 38 . Synthesis of 1,3‐oxazine‐2,4‐diones and their reaction with nucleophiles. Ring transformation of 1,3‐oxazines to pyrimidines
Author(s) -
Yogo Motoi,
Hirota Kosaku,
Senda Shigeo
Publication year - 1981
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.5570180607
Subject(s) - chemistry , ethylamine , aniline , sodium cyanide , ring (chemistry) , sodium azide , pyrimidine , morpholine , nucleophile , methylamine , medicinal chemistry , oxazines , sodium hydride , cyanide , organic chemistry , stereochemistry , catalysis
5,6‐Unsubstituted 1,3‐oxazine‐2,4‐diones ( 3 ) and 6‐unsubstituted 5‐methyl‐1,3‐oxazine‐2,4‐diones ( 4 ) were prepared by reduction of the corresponding 6‐chloro derivatives ( 1 and 2 ). Treatment of 6‐chloro‐3‐methyl‐1,3‐oxazine‐2,4‐dione ( 1a ) with sodium azide, sodium cyanide, secondary amines and aniline gave the corresponding 6‐substituted compounds ( 7, 9, 10 and 11 ) while the reaction of 1a and 2a,b with primary aliphatic amines such as methylamine and ethylamine caused a ring transformation to pyrimidine ring system giving barbituric acids ( 13a‐d ).