Formal Alkenylation and Amination of 2-Nitrobenzofurans with Fumaric Acid Amide Ester under Metal-Free Conditions

Gunda Ananda Rao; Paru Jamwal; Ramani Gurubrahamam; Kwunmin Chen

doi:10.1002/slct.202204467

Formal Alkenylation and Amination of 2-Nitrobenzofurans with Fumaric Acid Amide Ester under Metal-Free Conditions

Gunda Ananda Rao, Paru Jamwal, Ramani Gurubrahamam^*, Kwunmin Chen^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

摘要

An inorganic base promoted metal-free formal alkenylation and amination of 2-nitrobenzofurans is established with fumaric acid amide ester derivatives. The cascade strategy provides the 2-alkenyl and 3-amino substituted benzofurans via Michael addition/cyclization/nitrous acid elimination/N-demethoxylation/C−N bond cleavage and isomerization sequence. The desired 2-(3-aminobenzofuran-2-yl)malonate derivatives are obtained in moderate-to-good yields with high stereoselectivity under mild reaction conditions (up to 71 % yield and >20 : 1 Z : E). The structure of the products is assigned from the single crystal x-ray structural analysis.

原文	英語
文章編號	e202204467
期刊	ChemistrySelect
卷	8
發行號	1
DOIs	https://doi.org/10.1002/slct.202204467
出版狀態	已發佈 - 2023 1月 9

ASJC Scopus subject areas

一般化學

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10.1002/slct.202204467

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CCDC 2101295: Experimental Crystal Structure Determination
Ananda Rao, G. (Contributor), Jamwal, P. (Contributor), Gurubrahamam, R. (Contributor) & Chen, K. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc28jkq3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc28jkq3&sid=DataCite
資料集: Dataset

引用此

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title = "Formal Alkenylation and Amination of 2-Nitrobenzofurans with Fumaric Acid Amide Ester under Metal-Free Conditions",

abstract = "An inorganic base promoted metal-free formal alkenylation and amination of 2-nitrobenzofurans is established with fumaric acid amide ester derivatives. The cascade strategy provides the 2-alkenyl and 3-amino substituted benzofurans via Michael addition/cyclization/nitrous acid elimination/N-demethoxylation/C−N bond cleavage and isomerization sequence. The desired 2-(3-aminobenzofuran-2-yl)malonate derivatives are obtained in moderate-to-good yields with high stereoselectivity under mild reaction conditions (up to 71 % yield and >20 : 1 Z : E). The structure of the products is assigned from the single crystal x-ray structural analysis.",

keywords = "2-Nitrobenzofuran, Alkenylation, Amination, Furmaric acid amide ester, Nitrous acid elimination",

author = "{Ananda Rao}, Gunda and Paru Jamwal and Ramani Gurubrahamam and Kwunmin Chen",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

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T1 - Formal Alkenylation and Amination of 2-Nitrobenzofurans with Fumaric Acid Amide Ester under Metal-Free Conditions

AU - Ananda Rao, Gunda

AU - Jamwal, Paru

AU - Gurubrahamam, Ramani

AU - Chen, Kwunmin

PY - 2023/1/9

Y1 - 2023/1/9

N2 - An inorganic base promoted metal-free formal alkenylation and amination of 2-nitrobenzofurans is established with fumaric acid amide ester derivatives. The cascade strategy provides the 2-alkenyl and 3-amino substituted benzofurans via Michael addition/cyclization/nitrous acid elimination/N-demethoxylation/C−N bond cleavage and isomerization sequence. The desired 2-(3-aminobenzofuran-2-yl)malonate derivatives are obtained in moderate-to-good yields with high stereoselectivity under mild reaction conditions (up to 71 % yield and >20 : 1 Z : E). The structure of the products is assigned from the single crystal x-ray structural analysis.

AB - An inorganic base promoted metal-free formal alkenylation and amination of 2-nitrobenzofurans is established with fumaric acid amide ester derivatives. The cascade strategy provides the 2-alkenyl and 3-amino substituted benzofurans via Michael addition/cyclization/nitrous acid elimination/N-demethoxylation/C−N bond cleavage and isomerization sequence. The desired 2-(3-aminobenzofuran-2-yl)malonate derivatives are obtained in moderate-to-good yields with high stereoselectivity under mild reaction conditions (up to 71 % yield and >20 : 1 Z : E). The structure of the products is assigned from the single crystal x-ray structural analysis.

KW - 2-Nitrobenzofuran

KW - Alkenylation

KW - Amination

KW - Furmaric acid amide ester

KW - Nitrous acid elimination

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Formal Alkenylation and Amination of 2-Nitrobenzofurans with Fumaric Acid Amide Ester under Metal-Free Conditions

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 2101295: Experimental Crystal Structure Determination

引用此