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N,N′ ‐Cyclization of carbodiimides with 2‐(bromomethyl)acrylic acid. A direct entry to the system 5‐methylene‐6 H ‐pyrimidine‐2,4‐dione, a new class of thymine analogues
Author(s) -
Anglada J. M.,
Campos T.,
Camps F.,
Moretó J. M.,
Pagès L.L.
Publication year - 1996
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.5570330444
Subject(s) - chemistry , methylene , pyrimidine , nucleophile , acrylic acid , hydrochloric acid , bromine , organic chemistry , medicinal chemistry , stereochemistry , catalysis , polymer , monomer
Carbodiimides react under very mild conditions with 2‐(bromomethyl)acrylic acid at both N atoms to give 1,3‐disubstituted‐5‐methylene‐6 H ‐pyrimidine 2,4‐dione derivatives in moderate to good yields. These products behaved as good Michael acceptors towards a variety of nucleophiles such as bromine, hydrochloric acid, hydrides, etc . A plausible mechanism is proposed based on theoretical approaches and experimental results.