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Syntheses of 1,3,8,10,12‐pentazanaphthacene‐2,4,7,9‐(12 H ,3 H ,8 H ,10 H )‐tetraones (linear pyrimidine‐fused 5‐deazaflavins), 1,3,6,8,12‐pentazabenz[ a ]anthracene‐2,4,7,9(12 H ,3 H ,6 H ,8 H )‐tetraones(bent pyrimidine‐fused 5‐deazaflavins), and their flavin analogs
Author(s) -
Yoneda Fumio,
Koga Masakazu
Publication year - 1989
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.5570260111
Subject(s) - chemistry , pyrimidine , flavin group , reagent , anthracene , bent molecular geometry , stereochemistry , condensation , medicinal chemistry , photochemistry , organic chemistry , physics , thermodynamics , enzyme
1,3,8,10,12‐Pentazanaphthacene‐2,4,7,9(12 H ,3 H ,8 H ,10 H )‐tetraones (linear pyrimidine‐fused 5‐deazaflavins) and 1,3,6,8,12‐pentazabenz[ a ]anthracene‐2,4,7,9(12 H ,3 H ,6 H ,8 H )‐tetraones (bent pyrimidine‐fused 5‐deazaflavins) were synthesized by condensation of 7‐alkylaminoquinazoline with 6‐chloro‐5‐formyl‐3‐methyluracil. Also, their flavin analogs, 1,3,5,8,10,12‐hexazanaphthacene‐2,4,7,9(12 H ,3 H ,8 H ,10 H )‐tetraones (linear pyrimidine‐fused flavins) and l,3,5,6,8,12‐hexazabenz[ a ]anthracene‐2,4,7,9(12 H ,3 H ,6 H ,8 H )‐tetraones (bent pyrimidine‐fused flavins) were synthesized by cyclization of 7‐[ N ‐alkyl‐ N ‐(5‐nitrouracil‐6‐yl)]aminoquin‐azolines with the Vilsmeier reagent.