Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazoles
Herein we report a significant, valuable extension of a recently implemented pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C<sub>4</sub> building blocks, led to indole derivatives characterized by unusual patterns of substitution. The 6-n...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/20/3802 |
| _version_ | 1818339668003913728 |
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| author | Alice Benzi Lara Bianchi Massimo Maccagno Angela Pagano Giovanni Petrillo Cinzia Tavani |
| author_facet | Alice Benzi Lara Bianchi Massimo Maccagno Angela Pagano Giovanni Petrillo Cinzia Tavani |
| author_sort | Alice Benzi |
| collection | DOAJ |
| description | Herein we report a significant, valuable extension of a recently implemented pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C<sub>4</sub> building blocks, led to indole derivatives characterized by unusual patterns of substitution. The 6-nitro-7-arylindoles resulting from suitably derivatized, non-symmetric dienes are of foreseeable synthetic interest in search for new polyheterocyclic systems. As an example, pyrrolocarbazoles with a rarely reported ring fusion were synthesized with the classical Cadogan protocol. Furthermore, the proven easy reducibility of the nitro group to amine will surely open the way to further interesting elaborations. |
| first_indexed | 2024-12-13T15:30:39Z |
| format | Article |
| id | doaj.art-da9e801d6aab451a86377daa61f10e38 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T15:30:39Z |
| publishDate | 2019-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-da9e801d6aab451a86377daa61f10e382022-12-21T23:40:12ZengMDPI AGMolecules1420-30492019-10-012420380210.3390/molecules24203802molecules24203802Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazolesAlice Benzi0Lara Bianchi1Massimo Maccagno2Angela Pagano3Giovanni Petrillo4Cinzia Tavani5Department of Chemistry and Industrial Chemistry, Università di Genova, Via Dodecaneso 31, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, Università di Genova, Via Dodecaneso 31, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, Università di Genova, Via Dodecaneso 31, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, Università di Genova, Via Dodecaneso 31, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, Università di Genova, Via Dodecaneso 31, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, Università di Genova, Via Dodecaneso 31, I-16146 Genova, ItalyHerein we report a significant, valuable extension of a recently implemented pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C<sub>4</sub> building blocks, led to indole derivatives characterized by unusual patterns of substitution. The 6-nitro-7-arylindoles resulting from suitably derivatized, non-symmetric dienes are of foreseeable synthetic interest in search for new polyheterocyclic systems. As an example, pyrrolocarbazoles with a rarely reported ring fusion were synthesized with the classical Cadogan protocol. Furthermore, the proven easy reducibility of the nitro group to amine will surely open the way to further interesting elaborations.https://www.mdpi.com/1420-3049/24/20/3802nitroindolesnitrobutadienesbenzannulationmichael additioncadogan reaction |
| spellingShingle | Alice Benzi Lara Bianchi Massimo Maccagno Angela Pagano Giovanni Petrillo Cinzia Tavani Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazoles Molecules nitroindoles nitrobutadienes benzannulation michael addition cadogan reaction |
| title | Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazoles |
| title_full | Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazoles |
| title_fullStr | Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazoles |
| title_full_unstemmed | Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazoles |
| title_short | Sequential Annulations to Interesting Novel Pyrrolo[3,2-<i>c</i>]carbazoles |
| title_sort | sequential annulations to interesting novel pyrrolo 3 2 i c i carbazoles |
| topic | nitroindoles nitrobutadienes benzannulation michael addition cadogan reaction |
| url | https://www.mdpi.com/1420-3049/24/20/3802 |
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