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 building blocks, led to indole derivatives characterized by unusual patterns of substitution. The 6-nitro-7-arylindoles resul...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-10, Vol.24 (20), p.3802
Main Authors: Benzi, Alice, Bianchi, Lara, Maccagno, Massimo, Pagano, Angela, Petrillo, Giovanni, Tavani, Cinzia
Format: Article
Language:English
Subjects:
Aromatic compounds
benzannulation
Benzene
cadogan reaction
Carbazoles
Carbazoles - chemical synthesis
Carbazoles - chemistry
Hydrocarbons
Indoles
Indoles - chemical synthesis
Indoles - chemistry
michael addition
Model testing
Molecular Structure
nitrobutadienes
Nitrogen
nitroindoles
Pyrroles - chemical synthesis
Pyrroles - chemistry
Reaction time
Ring opening
Substrates
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Summary:Herein we report a significant, valuable extension of a recently implemented pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C 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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24203802