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Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]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(4) building blocks, led to indole derivatives characterized by unusual patterns of substitution. The 6-nitro-7-arylindoles re...

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Detalles Bibliográficos
Autores principales: Benzi, Alice, Bianchi, Lara, Maccagno, Massimo, Pagano, Angela, Petrillo, Giovanni, Tavani, Cinzia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6832463/
https://www.ncbi.nlm.nih.gov/pubmed/31652581
http://dx.doi.org/10.3390/molecules24203802
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author Benzi, Alice
Bianchi, Lara
Maccagno, Massimo
Pagano, Angela
Petrillo, Giovanni
Tavani, Cinzia
author_facet Benzi, Alice
Bianchi, Lara
Maccagno, Massimo
Pagano, Angela
Petrillo, Giovanni
Tavani, Cinzia
author_sort Benzi, Alice
collection PubMed
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(4) 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.
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spelling pubmed-68324632019-11-25 Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles Benzi, Alice Bianchi, Lara Maccagno, Massimo Pagano, Angela Petrillo, Giovanni Tavani, Cinzia Molecules Article Herein we report a significant, valuable extension of a recently implemented pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C(4) 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. MDPI 2019-10-22 /pmc/articles/PMC6832463/ /pubmed/31652581 http://dx.doi.org/10.3390/molecules24203802 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Benzi, Alice
Bianchi, Lara
Maccagno, Massimo
Pagano, Angela
Petrillo, Giovanni
Tavani, Cinzia
Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles
title Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles
title_full Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles
title_fullStr Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles
title_full_unstemmed Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles
title_short Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles
title_sort sequential annulations to interesting novel pyrrolo[3,2-c]carbazoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6832463/
https://www.ncbi.nlm.nih.gov/pubmed/31652581
http://dx.doi.org/10.3390/molecules24203802
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