Silver-catalyzed incorporation of carbon dioxide into o-alkynylaniline derivatives

Tomonobu Ishida; Satoshi Kikuchi; Tatsuyuki Tsubo; Tohru Yamada

doi:10.1021/ol303534w

Silver-catalyzed incorporation of carbon dioxide into o-alkynylaniline derivatives

Tomonobu Ishida, Satoshi Kikuchi, Tatsuyuki Tsubo, Tohru Yamada

Department of Chemistry

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

124 Citations (Scopus)

Abstract

Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though their synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, are required. It was found that a silver catalyst successfully promoted the incorporation of CO₂ into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at the activated C-C triple bond.

Original language	English
Pages (from-to)	848-851
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	4
DOIs	https://doi.org/10.1021/ol303534w
Publication status	Published - 2013 Feb 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol303534w

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abstract = "Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though their synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, are required. It was found that a silver catalyst successfully promoted the incorporation of CO2 into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at the activated C-C triple bond.",

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AU - Ishida, Tomonobu

AU - Kikuchi, Satoshi

AU - Tsubo, Tatsuyuki

AU - Yamada, Tohru

PY - 2013/2/15

Y1 - 2013/2/15

N2 - Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though their synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, are required. It was found that a silver catalyst successfully promoted the incorporation of CO2 into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at the activated C-C triple bond.

AB - Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though their synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, are required. It was found that a silver catalyst successfully promoted the incorporation of CO2 into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at the activated C-C triple bond.

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Silver-catalyzed incorporation of carbon dioxide into o-alkynylaniline derivatives

Abstract

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