Citation: 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. doi: 10.6023/cjoc201910016 shu

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

Corresponding author: Yan Chaoguo, cgyan@yzu.edu.cn
Received Date: 12 October 2019
Revised Date: 13 November 2019
Available Online: 2 December 2019
Fund Project: the National Natural Science Foundation of China 21572196Project supported by the National Natural Science Foundation of China (No. 21572196) and the Priority Academic Program Development of Jiangsu Higher Education Institutions

Figures(7)

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