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Photochemical functionalization of 6‐azauracils to 5‐substituted‐6‐azauracils
Author(s) -
Swenton John S.,
Balchunis Robert J.
Publication year - 1974
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.5570110612
Subject(s) - chemistry , yield (engineering) , cycloaddition , bicyclic molecule , enol , surface modification , derivative (finance) , bromine , organic chemistry , carbon fibers , photochemistry , combinatorial chemistry , catalysis , materials science , composite number , economics , financial economics , metallurgy , composite material
Photochemical cycloaddition of 6‐azauracil derivatives to enol acetates yields hydrolytically labile bicyclic azetidines which decompose in good to excellent yield to 5‐substituted‐5,6‐dihydro‐6‐azauracils. These compounds can in turn be oxidized by bromine to the 5‐substituted‐6‐azauracil. This reaction sequence has also been applied to 2′,3′,5′‐tri‐ o ‐benzoyl‐6‐azauridine resulting in a 60% overall yield of the functionalized nucleoside derivative. The three‐step procedure reported here affords a simple method for carboncarbon bond formation at the 5‐position of 6‐azauracil and may be applicable to other imines systems.