Title of article
Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems
Author/Authors
Trofimov، نويسنده , , Boris A. and Mal’kina، نويسنده , , Anastasiya G. and Nosyreva، نويسنده , , Valentina V. and Shemyakina، نويسنده , , Olesya A. and Albanov، نويسنده , , Alexander I. and Afonin، نويسنده , , Andrei V. and Kazheva، نويسنده , , Olga N. and Alexandrov، نويسنده , , Grigorii G. and Dyachenko، نويسنده , , Oleg A.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2012
Pages
4
From page
927
To page
930
Abstract
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[9.5.2.02,10.03,7.012,16]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.
Keywords
2-dihydropyridines , Tandem reaction , Diels–Alder cyclodimerization , 15-Dioxa-7 , 7.012 , 16]octadeca-8 , 10.03 , 17-dienes , Ethyl isonicotinate , Tertiary cyanoacetylenic alcohols , 1 , 4
Journal title
Tetrahedron Letters
Serial Year
2012
Journal title
Tetrahedron Letters
Record number
1880135
Link To Document