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

doi:10.6023/cjoc201910016

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 1003-1016.DOI: 10.6023/cjoc201910016 Previous Articles Next Articles

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

丁邦东^a, 姜业朝^a, 张瑜^b, 叶蓉^b, 孙晶^b, 颜朝国^b

a 扬州工业职业技术学院化学工程学院江苏扬州 225127;
b 扬州大学化学化工学院江苏扬州 225002

收稿日期:2019-10-12 修回日期:2019-11-13 发布日期:2020-05-06
通讯作者: 颜朝国 E-mail:cgyan@yzu.edu.cn
基金资助:
国家自然科学基金（No.21572196）和江苏省优势学科建设工程资助项目.

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

Ding Bangdong^a, Jiang Yechao^a, Zhang Yu^b, Ye Rong^b, Sun Jin^b, Yan Chaoguo^b

a College of Chemical Engineering, Yangzhou Polytechnic Institute, Yangzhou, Jiangsu 225127;
b College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002

Received:2019-10-12 Revised:2019-11-13 Published:2020-05-06
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572196) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

1. 201003S.pdf(3875KB)

Abstract

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

Cite this article

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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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

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