Synthesis of substituted anilinesviaa gold-catalyzed three-component reaction

Hirofumi Ueda; Ryota Yamamoto; Minami Yamaguchi; Hidetoshi Tokuyama

doi:10.1039/d0ob02018d

Synthesis of substituted anilinesviaa gold-catalyzed three-component reaction

Hirofumi Ueda, Ryota Yamamoto, Minami Yamaguchi, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

4 Citations (Scopus)

Abstract

A three-component reaction for the synthesis of substituted anilines by a gold(i)-catalyzed domino reaction was developed. Cationic gold catalysts selectively and sequentially activated two different alkynes, which were involved in pyrrole synthesis and subsequent Diels-Alder reaction. The sequential formal (3 + 2) annulation/Diels-Alder reaction of three components provided a variety of substituted anilines in a modular fashion. Moreover, utility of the aniline products was demonstrated by derivatization to substituted benzoxazines, which are pharmaceutically important heterocycles.

Original language	English
Pages (from-to)	765-769
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	4
DOIs	https://doi.org/10.1039/d0ob02018d
Publication status	Published - 2021 Jan 28

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of substituted anilinesviaa gold-catalyzed three-component reaction",

abstract = "A three-component reaction for the synthesis of substituted anilines by a gold(i)-catalyzed domino reaction was developed. Cationic gold catalysts selectively and sequentially activated two different alkynes, which were involved in pyrrole synthesis and subsequent Diels-Alder reaction. The sequential formal (3 + 2) annulation/Diels-Alder reaction of three components provided a variety of substituted anilines in a modular fashion. Moreover, utility of the aniline products was demonstrated by derivatization to substituted benzoxazines, which are pharmaceutically important heterocycles.",

author = "Hirofumi Ueda and Ryota Yamamoto and Minami Yamaguchi and Hidetoshi Tokuyama",

note = "Funding Information: This work was supported by the Drug Discovery and Life Science Research (BINDS) from AMED under Grant Number JP19am0101100j0003 and JSPS KAKENHI Grant Numbers JP18H04379 in Middle Molecular Strategy, JP18H04231 in Precisely Designed Catalysts with Customized Scaffolding, and JP18H04642 in Hybrid Catalysis, a Grant-in aid for Scientific Research (B) (18H02549) and (C) (17K08204). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2020.",

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doi = "10.1039/d0ob02018d",

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T1 - Synthesis of substituted anilinesviaa gold-catalyzed three-component reaction

AU - Ueda, Hirofumi

AU - Yamamoto, Ryota

AU - Yamaguchi, Minami

AU - Tokuyama, Hidetoshi

N1 - Funding Information: This work was supported by the Drug Discovery and Life Science Research (BINDS) from AMED under Grant Number JP19am0101100j0003 and JSPS KAKENHI Grant Numbers JP18H04379 in Middle Molecular Strategy, JP18H04231 in Precisely Designed Catalysts with Customized Scaffolding, and JP18H04642 in Hybrid Catalysis, a Grant-in aid for Scientific Research (B) (18H02549) and (C) (17K08204). Publisher Copyright: © The Royal Society of Chemistry 2020.

PY - 2021/1/28

Y1 - 2021/1/28

N2 - A three-component reaction for the synthesis of substituted anilines by a gold(i)-catalyzed domino reaction was developed. Cationic gold catalysts selectively and sequentially activated two different alkynes, which were involved in pyrrole synthesis and subsequent Diels-Alder reaction. The sequential formal (3 + 2) annulation/Diels-Alder reaction of three components provided a variety of substituted anilines in a modular fashion. Moreover, utility of the aniline products was demonstrated by derivatization to substituted benzoxazines, which are pharmaceutically important heterocycles.

AB - A three-component reaction for the synthesis of substituted anilines by a gold(i)-catalyzed domino reaction was developed. Cationic gold catalysts selectively and sequentially activated two different alkynes, which were involved in pyrrole synthesis and subsequent Diels-Alder reaction. The sequential formal (3 + 2) annulation/Diels-Alder reaction of three components provided a variety of substituted anilines in a modular fashion. Moreover, utility of the aniline products was demonstrated by derivatization to substituted benzoxazines, which are pharmaceutically important heterocycles.

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JO - Organic and Biomolecular Chemistry

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ER -

Synthesis of substituted anilinesviaa gold-catalyzed three-component reaction

Abstract

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