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Three-Component Reactions with 3-Phenyl 1-azabicyclo[1.1.0]butane, Dimethyl Dicyanofumarate, and Primary Aromatic Amines


Mloston, G; Heimgartner, H (2010). Three-Component Reactions with 3-Phenyl 1-azabicyclo[1.1.0]butane, Dimethyl Dicyanofumarate, and Primary Aromatic Amines. Heterocycles, 80(2):1091-1102.

Abstract

The three-component reaction of 3-phenyl-1-azabicyclo[1.1.0]butane (1a) with 2,3-dicyanofumarates (DCFM) and primary aromatic amines in dichloromethane at room temperature yielded mixtures of (Z)-2-arylamino-3-cyanofumarates (7) and the corresponding (E)-2-(azetidin-1-yl)-3-cyanomaleates (6) and (9). In the case of anisidine (8d), higher oligomers containing three or four azetidine residues, e.g. 10a, were also formed. With more nucleophilic aliphatic amines, only 1:1 adducts of type 7 were obtained. The reaction course can be rationalized by the formation of intermediate zwitterions (11) via addition of the N-nucleophiles onto DCFM. The results show that the nucleophilicity of 1a toward DCFM is lower than that of aliphatic amines but exceeds that of aromatic amines.

Abstract

The three-component reaction of 3-phenyl-1-azabicyclo[1.1.0]butane (1a) with 2,3-dicyanofumarates (DCFM) and primary aromatic amines in dichloromethane at room temperature yielded mixtures of (Z)-2-arylamino-3-cyanofumarates (7) and the corresponding (E)-2-(azetidin-1-yl)-3-cyanomaleates (6) and (9). In the case of anisidine (8d), higher oligomers containing three or four azetidine residues, e.g. 10a, were also formed. With more nucleophilic aliphatic amines, only 1:1 adducts of type 7 were obtained. The reaction course can be rationalized by the formation of intermediate zwitterions (11) via addition of the N-nucleophiles onto DCFM. The results show that the nucleophilicity of 1a toward DCFM is lower than that of aliphatic amines but exceeds that of aromatic amines.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:February 2010
Deposited On:19 Mar 2010 13:13
Last Modified:07 Dec 2017 01:47
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Rector of the University of Lodz, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.3987/COM-09-S(S)91

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