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

Antonia Iazzetti, Antonio Arcadi, Sandro Cacchi, Giancarlo Fabrizi, Francesca Ghirga, Antonella Goggiamani, Fabio Marinelli

Risultato della ricerca: Contributo in rivistaArticolo in rivista

Abstract

An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2-c]quinazolines is described. The Pd-catalyzed reaction of o-(oaminophenylethynyl) 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.
Lingua originaleEnglish
pagine (da-a)2411-2417
Numero di pagine7
RivistaBeilstein Journal of Organic Chemistry
Volume14
DOI
Stato di pubblicazionePubblicato - 2018

Keywords

  • Arylboronic acids
  • DMFDMA
  • Indoles
  • Indoloquinazolines
  • Quinazolines

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