Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom