Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems

Ethyl isonicotinate reacts with tertiary cyanoacetylenic alcohols under exceptionally mild conditions (room temperature, without catalyst or solvent) to afford novel polycondensed heterocyclic systems, 4,15-dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes, in 30–68% yields....

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Bibliographic Details
Published in:Tetrahedron letters 2012-02, Vol.53 (8), p.927-930
Main Authors: Trofimov, Boris A., Mal’kina, Anastasiya G., Nosyreva, Valentina V., Shemyakina, Olesya A., Albanov, Alexander I., Afonin, Andrei V., Kazheva, Olga N., Alexandrov, Grigorii G., Dyachenko, Oleg A.
Format: Article
Language:English
Subjects:
1,2-Dihydropyridines
4,15-Dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes
Alcohols
Asymmetry
Carbon
Catalysts
Diels–Alder cyclodimerization
Ethyl isonicotinate
Formations
Fragments
Solvents
Tandem reaction
Tertiary cyanoacetylenic alcohols
Tetrahedrons
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Summary:Ethyl isonicotinate reacts with tertiary cyanoacetylenic alcohols under exceptionally mild conditions (room temperature, without catalyst or solvent) to afford novel polycondensed heterocyclic systems, 4,15-dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes, in 30–68% yields. This tandem cyclization is regio- and stereospecific. Despite several asymmetric carbons (up to six) being present in the molecules, only one diastereomer is formed and both cyanomethylidene fragments possess exclusively Z-configuration. The tandem sequence includes the formation of 1,3-oxazolidino-1,2-dihydropyridines which undergo Diels–Alder cyclodimerization to give the final products.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.12.035