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Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles.

ABSTRACT: Herein we report a significant, valuable extension of a recently implemented pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C4 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.

SUBMITTER: Benzi A

PROVIDER: S-EPMC6832463 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Sequential Annulations to Interesting Novel Pyrrolo[3,2-c]carbazoles.

Benzi Alice A Bianchi Lara L Maccagno Massimo M Pagano Angela A Petrillo Giovanni G Tavani Cinzia C

Molecules (Basel, Switzerland) 20191022 20

Herein we report a significant, valuable extension of a recently implemented pyrrole benzannulation methodology that, employing versatile nitrodienes from our lab as useful C4 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 report ...[more]

PMID: 31652581

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