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A Novel Approach for the Solid‐Phase Organic Synthesis of 1, 3‐Disubstituted Uracils
Author(s) -
Wei MeiHong,
Lin ShuYing,
Sheng ShengRi,
Wang Qing,
Cai MingZhong
Publication year - 2010
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201000044
Subject(s) - chemistry , acrylate , hydrogen peroxide , solid phase synthesis , intramolecular force , cleavage (geology) , organic base , organic chemistry , polymer chemistry , copolymer , polymer , peptide , biochemistry , geotechnical engineering , fracture (geology) , engineering
A novel procedure for solid‐phase organic synthesis of 1, 3‐disubstituted uracils using a cyclization‐cleavage strategy from Wang‐acrylate resin, amines and isocyanates. An acrylate ester resin is reacted in turn with PhSeBr and primary amines in one‐pot to afford N ‐substituted α‐phenylseleno‐β‐aminoesters followed by treatment with isocyanates to form α‐phenylseleno‐β‐ureidoester resin. Following oxidation‐elimination with excess of 30% hydrogen peroxide and intramolecular cyclization cleavage of the Wang resin using potassium ethoxide as a base to furnish 1, 3‐disubstituted uracils in good yields (80‐86%) and high purities (92‐96%).