SYNTHESIS OF BIS-ANALOGS OF „FISCHER’S ALDEHYDE“ UNDER VILSMEIER REACTION CONDITIONS AND FORMATION OF DIPYRROLOBENZOQUINOXALINE LINE TRIMETHINE CIANINE.

Author: marina Trapaidze
Co-authors: Shota Samsoniya, Marina Trapaidze, Nino Nikoleishvili
Keywords: bisaldehyd, trimethine cyanine, Fischer’s base, formylation, indoloindole, Vilsmeiers complexe, dipyrrolobenzoquinoxaline
Annotation:

Formylation is studied of bifunctional analogs of Fischer’s Base of dipyrroloquinoxalines and indole indole series under Vilsmeier reaction conditions at different ratio of stratum and Vilsmeier complex (VC). An anomalous product trimethine cianine was isolated in the case of 1,4,5,8-tetrahydro-1,1,8,8-tetramethyl-2,7-dimethylidendipyrrolo[1,2,3-d,e:3,2,1-i,j]benzo[g]quinoxaline at 60 C and molar ratio of reagents 1:5, and diformyl derivative 2,7-di(formylmethyliden)-1,4,5,8-tetrahydro-1,1,8,8-tetramethyldipyrrolo[1,2,3-d,e:3,2,1-i,j]benzo¬[g]quinoxaline was obtained at 35 C with the yield 67% and large excess of VC (1:45). Isomerous “Fischer’s bases” of indole indole series undergo smooth formylation with formation of corresponding diformyl derivatives 2,7-di(formylmethyliden)-1,3,¬3,¬6,¬¬8,¬8-hexamethylindoline[7,6-g]indoline and 2,9- di(formylmethyliden)-1,1,¬3,¬¬¬¬8,10,10- hexamethylindoline [4,5-е]indoline.