Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal
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 di...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.14.218 |
| _version_ | 1818445104221782016 |
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| author | Antonio Arcadi Sandro Cacchi Giancarlo Fabrizi Francesca Ghirga Antonella Goggiamani Antonia Iazzetti Fabio Marinelli |
| author_facet | Antonio Arcadi Sandro Cacchi Giancarlo Fabrizi Francesca Ghirga Antonella Goggiamani Antonia Iazzetti Fabio Marinelli |
| author_sort | Antonio Arcadi |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-14T19:26:31Z |
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| id | doaj.art-500196ad501e4cc2a2ffc986ee94a2ce |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T19:26:31Z |
| publishDate | 2018-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-500196ad501e4cc2a2ffc986ee94a2ce2022-12-21T22:50:12ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-09-011412411241710.3762/bjoc.14.2181860-5397-14-218Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetalAntonio Arcadi0Sandro Cacchi1Giancarlo Fabrizi2Francesca Ghirga3Antonella Goggiamani4Antonia Iazzetti5Fabio Marinelli6Dipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 671010 Coppito (AQ), ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185, Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185, Rome, ItalyCenter for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185, Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185, Rome, ItalyDipartimento di Scienze Fisiche e Chimiche, Università di L’Aquila, Via Vetoio, 671010 Coppito (AQ), ItalyAn 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.https://doi.org/10.3762/bjoc.14.218arylboronic acidsDMFDMAindolesindoloquinazolinesquinazolines |
| spellingShingle | Antonio Arcadi Sandro Cacchi Giancarlo Fabrizi Francesca Ghirga Antonella Goggiamani Antonia Iazzetti Fabio Marinelli Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal Beilstein Journal of Organic Chemistry arylboronic acids DMFDMA indoles indoloquinazolines quinazolines |
| title | Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal |
| title_full | Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal |
| title_fullStr | Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal |
| title_full_unstemmed | Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal |
| title_short | Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal |
| title_sort | synthesis of indolo 1 2 c quinazolines from 2 alkynylaniline derivatives through pd catalyzed indole formation cyclization with n n dimethylformamide dimethyl acetal |
| topic | arylboronic acids DMFDMA indoles indoloquinazolines quinazolines |
| url | https://doi.org/10.3762/bjoc.14.218 |
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