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

doi:10.6023/cjoc201910016

摘要/Abstract

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.

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

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)-quino-lin-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.

Key words: heteroaromatic N-ylide, quinolinium bromide, 1,3-indanedione, spiro compound, [3+2] cycloaddition, diastereo-selectivity

引用此文

丁邦东, 姜业朝, 张瑜, 叶蓉, 孙晶, 颜朝国. 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[J]. 有机化学, 2020, 40(4): 1003-1016.

Ding Bangdong, Jiang Yechao, Zhang Yu, Ye Rong, Sun Jin, Yan Chaoguo. Synthesis of Indanone-Containing Heterocycles via Cycloaddition Reaction of Quinolinium Ylides with 1,3-Indanedione and 2-Arylidene-1,3-indanediones[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1003-1016.

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