A one pot synthesis of annulated carbazole analogs

Arasambattu K. Mohanakrishnan; Vasudevan Dhayalan; J. Arul Clement; Ramalingam Balamurugan Radhakrishnan Sureshbabu; Natarajan Senthil Kumar

doi:10.1016/j.tetlet.2008.07.036

A one pot synthesis of annulated carbazole analogs

Arasambattu K. Mohanakrishnan, Vasudevan Dhayalan, J. Arul Clement, Ramalingam Balamurugan Radhakrishnan Sureshbabu, Natarajan Senthil Kumar

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

22 Scopus citations

Abstract

A ZnBr₂-mediated arylation of N-protected 2/3-bromomethylindoles containing an electron-deficient malonylidene unit with arenes at 80 °C led to the formation of arylated products, which on unprecedented 1,5-sigmatropic rearrangement followed by electrocyclization and subsequent aromatization with loss of diethylmalonate furnished the corresponding annulated carbazoles in reasonable yields.

Original language	English
Pages (from-to)	5850-5854
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2008.07.036
State	Published - 6 Oct 2008
Externally published	Yes

Keywords

1,5-Sigmatropic rearrangement
Arenes
Arylation
Carbazoles
Electrocyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.07.036

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title = "A one pot synthesis of annulated carbazole analogs",

abstract = "A ZnBr2-mediated arylation of N-protected 2/3-bromomethylindoles containing an electron-deficient malonylidene unit with arenes at 80 °C led to the formation of arylated products, which on unprecedented 1,5-sigmatropic rearrangement followed by electrocyclization and subsequent aromatization with loss of diethylmalonate furnished the corresponding annulated carbazoles in reasonable yields.",

keywords = "1,5-Sigmatropic rearrangement, Arenes, Arylation, Carbazoles, Electrocyclization",

author = "Mohanakrishnan, {Arasambattu K.} and Vasudevan Dhayalan and {Arul Clement}, J. and Sureshbabu, {Ramalingam Balamurugan Radhakrishnan} and {Senthil Kumar}, Natarajan",

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AU - Mohanakrishnan, Arasambattu K.

AU - Dhayalan, Vasudevan

AU - Arul Clement, J.

AU - Sureshbabu, Ramalingam Balamurugan Radhakrishnan

AU - Senthil Kumar, Natarajan

PY - 2008/10/6

Y1 - 2008/10/6

N2 - A ZnBr2-mediated arylation of N-protected 2/3-bromomethylindoles containing an electron-deficient malonylidene unit with arenes at 80 °C led to the formation of arylated products, which on unprecedented 1,5-sigmatropic rearrangement followed by electrocyclization and subsequent aromatization with loss of diethylmalonate furnished the corresponding annulated carbazoles in reasonable yields.

AB - A ZnBr2-mediated arylation of N-protected 2/3-bromomethylindoles containing an electron-deficient malonylidene unit with arenes at 80 °C led to the formation of arylated products, which on unprecedented 1,5-sigmatropic rearrangement followed by electrocyclization and subsequent aromatization with loss of diethylmalonate furnished the corresponding annulated carbazoles in reasonable yields.

KW - 1,5-Sigmatropic rearrangement

KW - Arenes

KW - Arylation

KW - Carbazoles

KW - Electrocyclization

UR - http://www.scopus.com/inward/record.url?scp=50049095280&partnerID=8YFLogxK

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DO - 10.1016/j.tetlet.2008.07.036

M3 - Article

SN - 0040-4039

VL - 49

SP - 5850

EP - 5854

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

A one pot synthesis of annulated carbazole analogs

Abstract

Keywords

ASJC Scopus subject areas

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