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^*

^*Corresponding author for this work

Department of Chemistry

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

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.

Original language	English
Article number	e202204467
Journal	ChemistrySelect
Volume	8
Issue number	1
DOIs	https://doi.org/10.1002/slct.202204467
Publication status	Published - 2023 Jan 9

Keywords

2-Nitrobenzofuran
Alkenylation
Amination
Furmaric acid amide ester
Nitrous acid elimination

ASJC Scopus subject areas

General Chemistry

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10.1002/slct.202204467

Cite this

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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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doi = "10.1002/slct.202204467",

language = "English",

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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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DO - 10.1002/slct.202204467

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 2101295: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2101295: Experimental Crystal Structure Determination

Cite this