Purification of 2,3,6,7,10,11-hexamethoxytriphenylene and Preparation of hexakiscarbonylmethyl and hexakiscyanomethyl derivatives of 2,3,6,7,10,11-hexahydroxytriphenylene

摘要

Abstract: 2,3,6,7,10,11-Hexamethoxytriphenylene (1) was subjected to an improved purificationprocedure and demethylated to give 2,3,6,7,10,11- hexahydroxytriphenylene (2) as the relativelystable trihydrate. Compound 2 was alkylated with reactive halogen reagents giving 2,3,6,7,10,11- hexakis(cyanomethyl)triphenylene (3),2,3,6,7,10, 11-hexakis(N,N-diethylcarbamoylmethyloxy)triphenylene (4) and 2,3,6,7,10,11-hexakis ethoxycarbonyl- methyloxy)triphenylene (5). Reduction of 4 gave2,3,6,7,10,11-hexakis(diethylaminoethyloxy)triphenylene (6) and reduction of 5 followed by acetyla- tion gave ,3,6,7,10,11-hexakis acetyloxyethyloxy) triphenylene (7). Hydrolysis of 5 gave 2,3,6,7,10, 11-hexakis(carboxymethyloxy)triphenylene (8). Compound 8 could be converted to its coresponding active N-hydroxysuccinimide ester (9) by the DCC method. Compound 9 was found to be a versatile core molecule that could be coupled with glycine-t -butyl ester, L-phenylalanine and L-phenylalanine- t -butyl ester giving compounds 10, 11 and 12.