1. Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal
- Author
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Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, Francesca Ghirga, Antonio Arcadi, Antonia Iazzetti, and Fabio Marinelli
- Subjects
Indole formation ,Indoles ,Settore CHIM/06 - CHIMICA ORGANICA ,Arylboronic acids ,DMFDMA ,Indoloquinazolines ,Quinazolines ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,Catalysis ,lcsh:QD241-441 ,Dimethyl acetal ,chemistry.chemical_compound ,Aniline ,lcsh:Organic chemistry ,lcsh:Science ,010405 organic chemistry ,0104 chemical sciences ,arylboronic acids ,indoles ,indoloquinazolines ,quinazolines ,chemistry ,N dimethylformamide ,Dimethylformamide ,lcsh:Q - Abstract
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 ArN2+BF4−, that afforded 12-arylindolo[1,2-c]quinazolin-6(5H)-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.
- Published
- 2018
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