One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

Takafumi Kitawaki; Yoko Hayashi; Akiko Ueno; Noritaka Chida

doi:10.1016/j.tet.2006.04.087

One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

Takafumi Kitawaki, Yoko Hayashi, Akiko Ueno, Noritaka Chida

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

99 Citations (Scopus)

Abstract

The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2′-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented.

Original language	English
Pages (from-to)	6792-6801
Number of pages	10
Journal	Tetrahedron
Volume	62
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2006.04.087
Publication status	Published - 2006 Jul 17
Externally published	Yes

Keywords

Double N-arylation
Murrastifoline-A
N-Substituted carbazole
One-pot synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.04.087

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title = "One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A",

abstract = "The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2′-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented.",

keywords = "Double N-arylation, Murrastifoline-A, N-Substituted carbazole, One-pot synthesis",

author = "Takafumi Kitawaki and Yoko Hayashi and Akiko Ueno and Noritaka Chida",

note = "Funding Information: We thank Professor H. Furukawa (Meijo University, Nagoya, Japan) for providing us with spectral data of natural murrastifoline-A. We also thank Professor K. Nozaki (The University of Tokyo, Tokyo, Japan) for valuable discussions on the double N-arylation reaction. This work was partially supported by Grant-in-Aid for the 21st Century COE program {\textquoteleft}KEIO LCC{\textquoteright} from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

year = "2006",

month = jul,

day = "17",

doi = "10.1016/j.tet.2006.04.087",

language = "English",

volume = "62",

pages = "6792--6801",

journal = "Tetrahedron",

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number = "29",

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T1 - One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

AU - Kitawaki, Takafumi

AU - Hayashi, Yoko

AU - Ueno, Akiko

AU - Chida, Noritaka

N1 - Funding Information: We thank Professor H. Furukawa (Meijo University, Nagoya, Japan) for providing us with spectral data of natural murrastifoline-A. We also thank Professor K. Nozaki (The University of Tokyo, Tokyo, Japan) for valuable discussions on the double N-arylation reaction. This work was partially supported by Grant-in-Aid for the 21st Century COE program ‘KEIO LCC’ from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2006/7/17

Y1 - 2006/7/17

N2 - The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2′-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented.

AB - The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2′-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented.

KW - Double N-arylation

KW - Murrastifoline-A

KW - N-Substituted carbazole

KW - One-pot synthesis

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U2 - 10.1016/j.tet.2006.04.087

DO - 10.1016/j.tet.2006.04.087

M3 - Article

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SN - 0040-4020

VL - 62

SP - 6792

EP - 6801

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

Abstract

Keywords

ASJC Scopus subject areas

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