喹啉季铵盐和1,3-茚满二酮及2-芳亚甲基1,3-茚满二酮的环加成反应合成茚满酮类含氮杂环化合物  

Synthesis of Indanone-Containing Heterocycles via Cycloaddition Reaction of Quinolinium Ylides with 1,3-Indanedione and 2-Arylidene-1,3-indanediones

作　　者：丁邦东[1] 姜业朝[1] 张瑜[2] 叶蓉 孙晶[2] 颜朝国[2] Ding Bangdong;Jiang Yechao;Zhang Yu;Ye Rong;Sun Jin;Yan Chaoguo(College of Chemical Engineering,Yangzhou Polytechnic Institute,Yangzhou,Jiangsu 225127;College of Chemistry&Chemical Engineering,Yangzhou University,Yangzhou,Jiangsu 225002)

机构地区：[1]扬州工业职业技术学院化学工程学院,江苏扬州225127 [2]扬州大学化学化工学院,江苏扬州225002

出　　处：《有机化学》2020年第4期1003-1016,共14页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21572196);江苏省优势学科建设工程资助项目.

摘　　要：在三乙胺存在下,N-苯甲酰基甲基喹啉溴化物和1,3-茚满二酮在乙醇中于室温反应,主要产物为多取代二氢吡咯[1,2-a]喹啉,次要产物为2-(1-苯甲酰基甲基)喹啉-4-亚基)-1,3-茚满二酮.在相同条件下,N-苄基喹啉溴化物和1,3-茚满二酮在乙醇中于室温反应,主要产物则为2-(1-苯甲酰基甲基)喹啉-4-亚基)-1,3-茚满二酮.另一方面,N-苯甲酰基甲基和N-乙氧羰基甲基以及N-(对硝基苄基)喹啉溴化物和芳香醛,1,3-茚满二酮的三组分反应,在三乙胺存在下在乙醇中高效地生成螺[茚满-2,3'-吡咯[1,2-a]喹啉]衍生物,反应具有很好的非对映选择性.The triethylamine promoted cycloaddition reaction of N-phenacylquinolinium bromide with 1,3-indanedione gave functionalized dihydropyrrolo[1,2-a]quinolines as main products and 2-(1-(2-oxo-2-phenylethyl)-quinolin-4-ylidene)-indene-1,3-diones as minor products.The similar reaction with N-benzylquinolinium bromide gave 2-(1-(2-oxo-2-phenylethyl)-quinolin-4-ylidene)-indene-1,3-diones as major products.On the other hand,triethylamine promoted three-component reaction of N-phenacyl,N-ethoxycarbonylmethyl and N-(4-nitrobenzyl)quinolinium salts,aromatic aldehydes and 1,3-indanedione in ethanol at room temperature afforded functionalized spiro[indene-2,3'-pyrrolo[1,2-a]quinolone]s in good yields and with high diastereoselectivity.

关 键 词：氮杂芳烃伊立德 喹啉季铵盐 1 3-茚满二酮 螺环化合物 [3+2]环加成反应 非对映选择性 

分 类 号：O626[理学—有机化学] O621.3[理学—化学]