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 | Zendy

Anglada J. M. | Zendy; Campos T. | Zendy; Camps F. | Zendy; Moretó J. M. | Zendy; Pagès L.L. | Zendy

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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.

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