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An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2- c ]quinazolines is described. The Pd-catalyzed reaction of o -( o -aminophenylethynyl) trifluoroacetanilides with Ar-B(OH) 2 afforded 2-( o -aminophenyl)-3-arylindoles, that were converted to 12-arylindolo[1,2- c ]quinazolines by adding dimethylformamide dimethyl acetal (DMFDMA) to the reaction mixture after extractive work-up. This reaction outcome is different from the previously reported Pd-catalyzed sequential reaction of the same substrates with Ar-I, Ar-Br and ArN 2  + BF 4  - , that afforded 12-arylindolo[1,2- c ]quinazolin-6(5 H )-ones. Moreover, 12-unsubstituted indolo[1,2- c ]quinazolines can be obtained both by reacting 2-( o -aminophenyl)indoles with DMFDMA or by sequential Pd-catalyzed reaction of o -( o -aminophenylethynyl)aniline with DMFDMA.

beilstein journal of organic chemistry

Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal