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Synthesis of 10‐deazariboflavin and related 2,4‐Dioxopyrimido[4,5‐ b ]quinolines
Author(s) -
O'Brien Darrcll E.,
Weinslock Louis T.,
Cheng C. C.
Publication year - 1970
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.5570070114
Subject(s) - chemistry , barbituric acid , anhydrous , quinoline , condensation , hydrazine (antidepressant) , sodium carbonate , potassium carbonate , medicinal chemistry , organic chemistry , hydrate , sodium , chromatography , physics , thermodynamics
Condensation of substituted anthranilaldehydes with barbituric acid results in the formation of 2,4‐dioxopyrimido[4,5‐ b ]quinolines. Using this general synthetic approach, 7,8‐dimethyl‐2,4‐dioxo‐10‐ribityl‐2,3,4,10‐tetrahydropyrimido[4,5‐ b ]quinoline (10‐deazariboflavin) was prepared by the condensation of barbituric acid with 4,5‐dimethyl‐ N ‐ribitylanthranilaldehyde. The latter was obtained in situ by the treatment of 1‐[4,5‐dimethyl‐ N ‐(ribityl)anthraniloyl]‐2‐( p ‐toluenesulfonyl)hydrazine, prepared from 4,5‐dimethylanthranilic acid with anhydrous sodium carbonate.