Development of new, simple and general synthetic methods of useful heterocyclic compounds

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First, two new and efficient methods for the preparation of quinoline derivatives were developed. The first method is based on reactions of 2-isocyanostyrene derivatives with electrophiles, such as aldehydes, ketones, and aldehydes, in the presence of a Lewis acid. The second method is based on reactions of 2-isocyano-β-methoxystyrene derivatives with organolithiums and lithium dialkylamides. As an application of the former method, 11H-indolo[3,2-c]quinolines carrying a functional group at the 6-position were prepared by electorophile-mediated cyclization of 2-(2-isocyanophenyl)-1-methyl-1H-indole. As an application of the latter method, isoquinoline derivatives were prepared by reactions of 2-cyano-β-methoxystyrene derivatives with organolithiums and lithium dialkylamides.Next, new syntheses of heterocycke-fused quinines, such as 1H,5H-pyrano[3,4-f]indole-4,9-dione,12-hydroxy-12H-thioxanthene-6,11-dione,thieno[2,3-f]benzofuran-4,8-dione,thieno[3,2-g]benzofuran-4,5-dione, and naphtho[1,2-b]thiophene-4,5-dione derivatives, were accomplishedFurthermore, utilizing reactions of various enolates with lactones and nitriles, 3,6,7,8-tetrahydro[3,2-c]oxepin-4(2H)-one, (3-iminoisoindolin-1-ylidene)carboxylic ester, and 3-(1-aminoalkyl)quinolin-2(1H)-one derivatives were prepared.Lastly, benzazetine and 4H-1,3-benzodioxin-2-one derivatives were prepared by iodocyclization of appropriately o-substituted styrene derivatives.