Efficient access to β- and γ-carbolines from a common starting material by sequential site-selective Pd-catalyzed C–C, C–N coupling reactions

Two efficient and practical approaches are reported for the synthesis of β- and γ-carboline derivatives from 3,4-dibromopyridine as a common starting material. The β-carbolines were prepared by site-selective Pd-catalyzed C–C coupling with o-bromophenylboronic acid and subsequent cyclization by doub...

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Bibliographic Details
Published in:	Tetrahedron Vol. 75; no. 40; p. 130569
Main Authors:	Hung, Tran Quang, Hieu, Do Trung, Van Tinh, Dinh, Do, Ha Nam, Nguyen Tien, Tuan Anh, Van Do, Dang, Son, Le Thanh, Tran, Ngoc Han, Van Tuyen, Nguyen, Tan, Vu Minh, Ehlers, Peter, Dang, Tuan Thanh, Langer, Peter
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 04-10-2019
Subjects:	Carbolines Catalysis Cyclizations Heterocycles Palladium Regioselectivity Heterocycles Carbolines Palladium Catalysis Cyclizations Regioselectivity
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Summary:	Two efficient and practical approaches are reported for the synthesis of β- and γ-carboline derivatives from 3,4-dibromopyridine as a common starting material. The β-carbolines were prepared by site-selective Pd-catalyzed C–C coupling with o-bromophenylboronic acid and subsequent cyclization by double C–N coupling with amines. γ-Carbolines were prepared from the same starting material by C–N coupling with anilines and subsequent annulation by domino C–C/C–N coupling with o-bromophenylboronic acid. [Display omitted] •β- and γ-carboline derivatives were prepared from a common starting material.•The reactions proceed with excellent regioselectivity.•High yields were obtained under optimized conditions.
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2019.130569