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

首先，开发了两种新的高效制备喹啉类化合物的方法。第一种方法是基于2-异氰基苯乙烯衍生物在Lewis酸存在下与亲电性物质，如醛、酮和醛的反应。第二种方法是基于2-异氰基-β-甲氧基苯乙烯衍生物与有机硫和二烷基胺锂的反应。作为前者的应用，通过亲电催化环化2-(2-异氰苯基)-1-甲基-1H-吲哚，合成了6-位带有官能团的11H-吲哚并[3，2-c]喹啉类化合物。作为后一种方法的应用，通过2-氰基-β-甲氧基苯乙烯衍生物与有机锂和二烷胺的反应合成了异喹啉衍生物。其次，利用不同烯醇类化合物与内酮和腈的反应，合成了新的杂环稠合奎宁，如Thieno[2，3-f]苯并呋喃-4，8-二酮、Thieno[3，2-g]苯并呋喃-4，5-二酮和萘并[1，2-b]噻吩二酮衍生物合成了7，8-四氢[3，2-c]奥西平-4(2H)-酮、(3-亚氨基异吲哚-1-亚甲基)羧酸酯和3-(1-氨基烷基)喹啉-2(1H)-酮衍生物。

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.