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


丁邦东a, 姜业朝a, 张瑜b, 叶蓉b, 孙晶b, 颜朝国b   

  1. 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
  • 基金资助:

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

Ding Bangdonga, Jiang Yechaoa, Zhang Yub, Ye Rongb, Sun Jinb, Yan Chaoguob   

  1. 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.

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