z-logo
Premium
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 ).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom