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Two- and Three-Component Reactions Leading to New Enamines Derived from 2,3-Dicyanobut-2-enoates


Mloston, G; Celeda, M; Linden, A; Heimgartner, H (2009). Two- and Three-Component Reactions Leading to New Enamines Derived from 2,3-Dicyanobut-2-enoates. Helvetica Chimica Acta, 92(8):1520-1537.

Abstract

The three-component reactions of 1-azabicyclo[1.1.0]butanes 1, dicyanofumarates (E)-5, and MeOH or morpholine yielded azetidine enamines 8 and 9 with the cis-orientation of the ester groups at the C=C bond ((E)-configuration; Schemes 3 and 4). The structures of 8a and 9d were confirmed by X-ray crystallography. The formation of the products is explained via the nucleophilic addition of 1 onto (E)-5, leading to a zwitterion of type 7 (Scheme 2), which is subsequently trapped by MeOH or morpholine (10a), followed by elimination of HCN. Similarly, two-component reactions between secondary amines 10a – 10c and (E)-5 gave products 12 with an (E)-enamine structure and (Z)-oriented ester groups. On the other hand, two-component reactions involving primary amines 10d – 10f or NH3 led to the formation
of the corresponding (Z)-enamines, in which the (E)-orientation of ester groups was established.

The three-component reactions of 1-azabicyclo[1.1.0]butanes 1, dicyanofumarates (E)-5, and MeOH or morpholine yielded azetidine enamines 8 and 9 with the cis-orientation of the ester groups at the C=C bond ((E)-configuration; Schemes 3 and 4). The structures of 8a and 9d were confirmed by X-ray crystallography. The formation of the products is explained via the nucleophilic addition of 1 onto (E)-5, leading to a zwitterion of type 7 (Scheme 2), which is subsequently trapped by MeOH or morpholine (10a), followed by elimination of HCN. Similarly, two-component reactions between secondary amines 10a – 10c and (E)-5 gave products 12 with an (E)-enamine structure and (Z)-oriented ester groups. On the other hand, two-component reactions involving primary amines 10d – 10f or NH3 led to the formation
of the corresponding (Z)-enamines, in which the (E)-orientation of ester groups was established.

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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:18 August 2009
Deposited On:25 Nov 2009 14:22
Last Modified:05 Apr 2016 13:33
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Rector of the University of Lodz, F. Hoffmann-La Roche AG, Basel
Additional Information:Free access at official URL
Publisher DOI:https://doi.org/10.1002/hlca.200900101
Official URL:http://www3.interscience.wiley.com/cgi-bin/fulltext/122563992/PDFSTART
Permanent URL: https://doi.org/10.5167/uzh-23956

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