Organic Letters

, volume 20 , issue 16 , pages 4759-4763

Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates

T. Mandal ¹

Gargi Chakraborti ¹

Shilpi KARMAKAR ¹

Jyotirmayee Dash ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India |

Publication type: Journal Article

Publication date: 2018-08-09

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.8b01827

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PubMed ID: 30091929

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2- a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.

Found

1 citation

Lvov Andrey

DSc in Chemistry

79 publications, 1 121 citations, 32 reviews

h-index: 20

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Irkutsk National Research Technical University

Research interests

Heterocyclic compounds

Organic Chemistry

Photochemistry

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GOST |

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Mandal T. et al. Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates // Organic Letters. 2018. Vol. 20. No. 16. pp. 4759-4763.

GOST all authors (up to 50) Copy

Mandal T., Chakraborti G., KARMAKAR S., Dash J. Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates // Organic Letters. 2018. Vol. 20. No. 16. pp. 4759-4763.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.8b01827

UR - https://doi.org/10.1021/acs.orglett.8b01827

TI - Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates

T2 - Organic Letters

AU - Mandal, T.

AU - Chakraborti, Gargi

AU - KARMAKAR, Shilpi

AU - Dash, Jyotirmayee

PY - 2018

DA - 2018/08/09

PB - American Chemical Society (ACS)

SP - 4759-4763

IS - 16

VL - 20

PMID - 30091929

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2018_Mandal,

author = {T. Mandal and Gargi Chakraborti and Shilpi KARMAKAR and Jyotirmayee Dash},

title = {Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates},

journal = {Organic Letters},

year = {2018},

volume = {20},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/acs.orglett.8b01827},

number = {16},

pages = {4759--4763},

doi = {10.1021/acs.orglett.8b01827}

}

MLA

Cite this

MLA Copy

Mandal, T., et al. “Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates.” Organic Letters, vol. 20, no. 16, Aug. 2018, pp. 4759-4763. https://doi.org/10.1021/acs.orglett.8b01827.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)