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Synthesis of 8‐substituted 5‐deazaflavins
Author(s) -
Link P. A. J.,
Van Der Pias H. C.,
Müller F.
Publication year - 1985
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.5570220347
Subject(s) - chemistry , bathochromic shift , reagent , condensation , medicinal chemistry , photochemistry , organic chemistry , fluorescence , physics , quantum mechanics , thermodynamics
To obtain 5‐deazaflavins exhibiting red‐shifted light absorption spectra, a number of C(8) substituted 5‐deazaisoalloxazines were synthesized. This was accomplished a) by the oxidative cyclization of 5,5′‐arylmethylenebis(6‐methylaminouracil) derivatives and b) by the cyclization of N ‐methylanilinouracil derivatives with a one‐carbon reagent. The latter method led to the formation of impure products. Condensation and oxidation reactions with the π‐electron deficient C(8) methyl group in 5‐deazalumiflavin did not occur. Introduction of substituents at the C(8) position caused a bathochromic shift that varied between 10 and 40 nm.