SYNTHETIC SPECTROSCOPIC MODELS RELATED TO COENZYMES AND BASE PAIRS .6. SYNTHESIS OF (OMEGA-ARYLALKYL)-6,7-DIMETHYLISOALLOXAZINES, SPECTROSCOPIC MODEL COMPOUNDS RELATED TO FLAVIN-ADENINE DINUCLEOTIDE

A general method has been employed for the synthesis of 9-(ω-arylalkyl)-6,7-dimethylisoalloxazines (1) in which the flavin and arene nuclei are linked by n = 2, 3, and 6 methylene groups. These compounds serve as spectroscopic models for the study of interactions between the terminal rings as a function of separation and conformation. The following have been prepared: 9-[2-(aden-9-yl)ethyl]-6,7-dimethylisoalloxazine, Fl-C2-Ad (1a, n = 2), 9-[3-(aden-9-yl)propyl]-6,7-dimethylisoalloxazine, Fl-C3-Ad (1a, n = 3), and 9-[6-(aden-9-yl)-hexyl]-6,7-dimethylisoalloxazine, Fl-C2-Ad (1a, n = 6); 6,7-dimethyl-9-[2-(3-indolyl)ethyl]isoalloxazine, Fl-C2-Ind (1b, n = 2), and 6,7-dimethyl-9-[3-(3-indolyl)propyl]isoalloxazine, Fl-C3-Ind (1b, n = 3); trimethylenebis- 9,9′-(6,7-dimethylisoalloxazine), Fl-C2-Fl (1c, n = 3), and hexamethylenebis-9,9′-(6,7-dimethylisoalloxazine, Fl-C6-Fl (1c, n = 6); 6,7-dimethyl-9-(3,4,5-trimethoxybenzyl)isoalloxazine, Fl-C1-TMB (1d, n = 1), and 6,7-dimethyl-9-(3,4,5-trimethoxyphenethyl)isoalloxazine, Fl-C2-TMB (1d, n = 2). © 1969, American Chemical Society. All rights reserved.