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Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems |
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| Authors: | Boris A Trofimov Anastasiya G Mal’kinaValentina V Nosyreva Olesya A ShemyakinaAlexander I Albanov Andrei V AfoninOlga N Kazheva Grigorii G AlexandrovOleg A Dyachenko |
| Institution: | a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia b Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Academician N.N. Semenov Str., Chernogolovka 142432, Russia c N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninskii Prosp., Moscow 119991, Russia |
| 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-diazapentacyclo9.5.2.02,10.03,7.012,16]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: | Ethyl isonicotinate Tertiary cyanoacetylenic alcohols 1 2-Dihydropyridines Tandem reaction Diels-Alder cyclodimerization 4 15-Dioxa-7 12-diazapentacyclo[9 5 2 02 10 03 7 012 16]octadeca-8 17-dienes |
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