Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis and Properties of 2, 3, 4, 8-Tetrahydro-2, 4-dioxopyrido [2, 3-d]-pyrimidines (5-Deazalumazines) and Their Bis-compounds
TOMOHISA NAGAMATSUMASAKAZU KOGAFUMIO YONEDA
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Keywords: 5-deazalumazine
JOURNAL FREE ACCESS

1984 Volume 32 Issue 5 Pages 1699-1708

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Abstract

Ethyl 2, 3, 4, 8-tetrahydro-3-methyl-2, 4-dioxopyrido [2, 3-d] pyrimidine-6-carboxylates (IV) and their bis-compounds (VI) were synthesized by the condensation of 6-alkyl-or 6-aryl-amino-3-methyluracils (II) and appropriate ethyl 3-chloro-2-formylprop-2-enoates (III) in dimethylformamide. Hydrolysis of the esters IV and VI with base resulted in a novel rearrangement of a substituent (R2) at the 7-position onto the 6-substituent to give the corresponding 6-acyl-1, 2, 3, 4, 7, 8-hexahydro-3-methyl-2, 4, 7-trioxopyrido [2, 3-d] pyrimidines (VII) and their bis-compounds (X). The mechanism of the rearrangement is discussed.

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© The Pharmaceutical Society of Japan
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