2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond

Antonio Lorente; Marta Casillas; Pilar Gómez-Sal; Antonio Manzanero

doi:10.1139/v96-032

journal article Mar 01, 1996

2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond

Antonio Lorente Marta Casillas Pilar Gómez-Sal Antonio Manzanero

Canadian Journal of Chemistry Vol. 74 No. 3 pp. 287-294 · Canadian Science Publishing

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Abstract

The synthesis of (E)-1-methoxy-2-azabuta-1,3-diene-4-carbonitriles was performed by methylation of N-alkenylamides 9 and 11. The Z isomers were obtained by treatment of (E)-1-methylthio-2-azabuta-1,3-diene-4,4-dicarbonitriles with sodium methoxide in methanol. We also describe the reactions of (E)-1-methylthio-2-azabuta-1,3-diene-4,4-dicarbonitriles with pyrrolidine, which afforded 1-(1-pyrrolidinyl) derivatives 20, 21, and 23. X-ray crystallographic analyses of 21 and 23 established the E stereochemistry of the C—N double bond. Key words: 2-azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis, nucleophilic substitution and X-ray diffraction; N-alkenylamides: methylation.

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Details

Published: Mar 01, 1996
Vol/Issue: 74(3)
Pages: 287-294
License: View

Authors

Departamento de Química Inorgánica, Campus Universitario, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain

A

Antonio Manzanero

Cite This Article

Antonio Lorente, Marta Casillas, Pilar Gómez-Sal, et al. (1996). 2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond. Canadian Journal of Chemistry, 74(3), 287-294. https://doi.org/10.1139/v96-032

2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond

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