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New routes to 1‐deoxy‐(3,4‐dihydro‐7,8‐dimethyl‐2,4‐dioxopyrimido[4,5‐ b ]‐quinolin‐10(2 H )yl)‐D‐ribitols (5‐deazariboflavins)
Author(s) -
Ashton Wallace T.,
Brown Ronald D.,
Tolman Richard L.
Publication year - 1978
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.5570150324
Subject(s) - chemistry , derivative (finance) , chloride , uracil , acetylation , acetyl chloride , medicinal chemistry , methyl formate , organic chemistry , formate , catalysis , biochemistry , dna , financial economics , economics , gene
The acid‐catalyzed reaction of 6‐( N ‐D‐ribityl‐3,4‐xylidino)uracil ( 1 ) with trimethyl ortho‐formate yields a bis(methoxymethylene) derivative ( 2 ), which is readily deprotected to give 5‐deazariboflavin ( 3 ). Correspondingly, 5‐methyl‐5‐deazariboflavin ( 6 ) is produced by cyclization of the tetraacetate of 1 with acetyl chloride in the presence of stannic chloride followed by deacetylation.