Mechanism-controlled regioselective synthesis of indolyl benzo[b]carbazoles

David St C. Black; Donald C. Craig; Mardi Santoso

doi:10.1016/S0040-4039(99)01268-X

Mechanism-controlled regioselective synthesis of indolyl benzo[b]carbazoles

David St C. Black
, Donald C. Craig
, Mardi Santoso

University of New South Wales

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

14 Citations (Scopus)

Abstract

Benzo[b]carbazoles can be synthesised readily and in good yields from the combination of 2,3-unsubstituted indoles and o-phthaldialdehyde in the presence of acid catalysts. Use of phosphoryl chloride in chloroform gives rapid reactions and yields 11-(3-indolyl)benzo[b]carbazoles, whereas the use of p-toluenesulfonic acid in methanol gives slow reactions and yields the isomeric 6-(3-indolyl)benzo[b]carbazoles.

Original language	English
Pages (from-to)	6653-6656
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(99)01268-X
Publication status	Published - 3 Sept 1999
Externally published	Yes

Keywords

Antitumour compounds
Indoles
Polycyclic heterocyclic compounds
Regioselectivity

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10.1016/S0040-4039(99)01268-X

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title = "Mechanism-controlled regioselective synthesis of indolyl benzo[b]carbazoles",

abstract = "Benzo[b]carbazoles can be synthesised readily and in good yields from the combination of 2,3-unsubstituted indoles and o-phthaldialdehyde in the presence of acid catalysts. Use of phosphoryl chloride in chloroform gives rapid reactions and yields 11-(3-indolyl)benzo[b]carbazoles, whereas the use of p-toluenesulfonic acid in methanol gives slow reactions and yields the isomeric 6-(3-indolyl)benzo[b]carbazoles.",

keywords = "Antitumour compounds, Indoles, Polycyclic heterocyclic compounds, Regioselectivity",

author = "Black, \{David St C.\} and Craig, \{Donald C.\} and Mardi Santoso",

year = "1999",

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day = "3",

doi = "10.1016/S0040-4039(99)01268-X",

language = "English",

volume = "40",

pages = "6653--6656",

journal = "Tetrahedron Letters",

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number = "36",

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TY - JOUR

T1 - Mechanism-controlled regioselective synthesis of indolyl benzo[b]carbazoles

AU - Black, David St C.

AU - Craig, Donald C.

AU - Santoso, Mardi

PY - 1999/9/3

Y1 - 1999/9/3

N2 - Benzo[b]carbazoles can be synthesised readily and in good yields from the combination of 2,3-unsubstituted indoles and o-phthaldialdehyde in the presence of acid catalysts. Use of phosphoryl chloride in chloroform gives rapid reactions and yields 11-(3-indolyl)benzo[b]carbazoles, whereas the use of p-toluenesulfonic acid in methanol gives slow reactions and yields the isomeric 6-(3-indolyl)benzo[b]carbazoles.

AB - Benzo[b]carbazoles can be synthesised readily and in good yields from the combination of 2,3-unsubstituted indoles and o-phthaldialdehyde in the presence of acid catalysts. Use of phosphoryl chloride in chloroform gives rapid reactions and yields 11-(3-indolyl)benzo[b]carbazoles, whereas the use of p-toluenesulfonic acid in methanol gives slow reactions and yields the isomeric 6-(3-indolyl)benzo[b]carbazoles.

KW - Antitumour compounds

KW - Indoles

KW - Polycyclic heterocyclic compounds

KW - Regioselectivity

UR - https://www.scopus.com/pages/publications/0033520207

U2 - 10.1016/S0040-4039(99)01268-X

DO - 10.1016/S0040-4039(99)01268-X

M3 - Article

AN - SCOPUS:0033520207

SN - 0040-4039

VL - 40

SP - 6653

EP - 6656

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Mechanism-controlled regioselective synthesis of indolyl benzo[b]carbazoles

Abstract

Keywords

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