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.
Item Type: | Journal Article, refereed, original work |
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Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
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Dewey Decimal Classification: | 540 Chemistry |
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Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry |
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Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
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Language: | English |
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Date: | 18 August 2009 |
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Deposited On: | 25 Nov 2009 14:22 |
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Last Modified: | 08 Jul 2025 03:33 |
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Publisher: | Wiley-Blackwell Publishing, Inc. |
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ISSN: | 0018-019X |
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Funders: | Rector of the University of Lodz, F. Hoffmann-La Roche AG, Basel |
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Additional Information: | Free access at official URL |
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OA Status: | Closed |
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Publisher DOI: | https://doi.org/10.1002/hlca.200900101 |
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Official URL: | http://www3.interscience.wiley.com/cgi-bin/fulltext/122563992/PDFSTART |
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