A versatile synthesis of annulated carbazole analogs involving a domino reaction of bromomethylindoles with arenes/heteroarenes

Vasudevan Dhayalan; J. Arul Clement; Radhakrishnan Jagan; Arasambattu K. Mohanakrishnan

doi:10.1002/ejoc.200801018

A versatile synthesis of annulated carbazole analogs involving a domino reaction of bromomethylindoles with arenes/heteroarenes

Vasudevan Dhayalan, J. Arul Clement, Radhakrishnan Jagan, Arasambattu K. Mohanakrishnan

Research output: Contribution to journal › Article › peer-review

60 Scopus citations

Abstract

A ZnBr₂-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80°C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatiza tion with loss of a diethylmalonate unit to afford the corresponding annulated products.

Original language	English
Pages (from-to)	531-546
Number of pages	16
Journal	European Journal of Organic Chemistry
Issue number	4
DOIs	https://doi.org/10.1002/ejoc.200801018
State	Published - 1 Feb 2009
Externally published	Yes

Keywords

Alkaloids
Annulation
Arenes
Cyclization
Sigmatropic rearrangement

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200801018

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abstract = "A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80°C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatiza tion with loss of a diethylmalonate unit to afford the corresponding annulated products.",

keywords = "Alkaloids, Annulation, Arenes, Cyclization, Sigmatropic rearrangement",

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AU - Clement, J. Arul

AU - Jagan, Radhakrishnan

AU - Mohanakrishnan, Arasambattu K.

PY - 2009/2/1

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N2 - A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80°C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatiza tion with loss of a diethylmalonate unit to afford the corresponding annulated products.

AB - A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80°C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatiza tion with loss of a diethylmalonate unit to afford the corresponding annulated products.

KW - Alkaloids

KW - Annulation

KW - Arenes

KW - Cyclization

KW - Sigmatropic rearrangement

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JF - European Journal of Organic Chemistry

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A versatile synthesis of annulated carbazole analogs involving a domino reaction of bromomethylindoles with arenes/heteroarenes

Abstract

Keywords

ASJC Scopus subject areas

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