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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 1003 - 1016

DOI: https://doi.org/10.6023/cjoc201910016

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

  • Ding Bangdong ,
  • Jiang Yechao ,
  • Zhang Yu ,
  • Ye Rong ,
  • Sun Jin ,
  • Yan Chaoguo
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  • a College of Chemical Engineering, Yangzhou Polytechnic Institute, Yangzhou, Jiangsu 225127;
    b College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002

Received date: 2019-10-12

  Revised date: 2019-11-13

  Online 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.

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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 . DOI: 10.6023/cjoc201910016

References

[1] (a) Addla, D.; Bhima; Sridhar, B.; Devi, A.; Kantevari, S. Bioorg. Med. Chem. Lett. 2012, 22, 7475.
(b) Chakrabarty, S.; Croft, M. S.; Marko, M. G.; Moyna, G. Bioorg. Med. Chem. 2013, 21, 1143/
(c) Muscia, G. C.; Buldain, G. Y.; Asis, S. E. Eur. J. Med. Chem. 2014, 73, 243.
[2] (a) Huang, H.-H.; Prabhakar, Ch.; Tang, K.-C.; Chou, P. T.; Huang, G. J.; Yang, J. S. J. Am. Chem. Soc. 2011, 133, 8028.
(b) Gomez-Esteban, S.; Benito-Hernandez, A.; Termine, R.; Hennrich, G.; Navarrete, J. T. L.; Ruiz Delgado, M. C.; Golemme, A.; Gomez-Lor, B. Chem.-Eur. J. 2018, 24, 3576.
(c) Sanguinet, L.; Williams, J. C.; Yang, Z. Y.; Twieg, R. J.; Mao, G. L.; Singer, K. D.; Wiggers, G.; Petschek, R. G. Chem. Mater. 2006, 18, 425.
[3] (a) Mondal, A.; Mukhopadhyay, C. ACS Comb. Sci. 2015, 17, 404.
(b) Mondal, A.; Banerjee, B.; Bhaumik, A.; Mukhopadhyay, C. ChemCatChem 2016, 8, 1185.
(c) Xu, H.; Chen, K.; Liu, H. W.; Wang, G. W. Org. Chem. Front. 2018, 5, 2864.
(d) Hussein, E. M.; Moussa, Z.; Ahmed, S. A. Monatsh. Chem. 2018, 149, 2021.
[4] (a) Zhou, Y. J.; Chen, D. S.; Li, Y. L.; Liu, Y.; Wang, X. S. ACS Comb. Sci. 2013, 15, 498.
(b) Chen, M.; Sun, N.; Liu, Y. H. Org. Lett. 2013, 15, 5574.
(c) Allais, C.; Lieby-Muller, F.; Rodriguez, J.; Constantieux, T. Eur. J. Org. Chem. 2013, 4131.
(d) Marquise, N.; Dorcet, V.; Chevallier, F.; Mongin, F. Org. Biomol. Chem. 2014, 12, 8138.
[5] (a) Mei, G. J.; Shi, F.; Chem. Commun. 2018, 54, 6607.
(b) Mei, G. J.; Li, D.; Zhou, G. X.; Shi, F.; Cao, Z. Chem. Commun. 2017, 53, 10030.
(c) Wu, J. L.; Du, B. X.; Zhang, Y. C.; He, Y. Y.; Wang, J. Y.; Wu, P.; Shi, F. Adv. Synth. Catal. 2016, 358, 2777.
(d) Zhu, Q. N.; Zhang, Y. C.; Xu, M. M.; Sun, X. X.; Yang, X.; Shi, F. J. Org. Chem. 2016, 81, 7898.
(e) Zhao, K.; Zhi, Y.; Shu, T.; Valkonen, A.; Rissanen, K.; Enders, D. Angew. Chem., Int. Ed. 2016, 55, 12104.
(f) Abbaraju, S.; Ramireddy, N.; Rana, N. K.; Arman, H. J.; Zhao, C. G. Adv. Synth. Catal. 2015, 357, 2633.
[6] (a) Abdukader, A.; Zhang, Y. H.; Zhang, Z. P.; Liu, C. J. Chin. J. Org. Chem. 2016, 36, 875(in Chinese). (阿布力米提·阿布都卡德尔, 张永红, 张增鹏, 刘晨江, 有机化学, 2016, 36, 875.)
(b) Tian, W. Y.; Xu, S.; Liang, Z. W.; Sun, D. L.; Zhang, R. H. Chin. J. Org. Chem. 2016, 36, 2121(in Chinese). (田文艳, 徐松, 梁中卫, 孙德立, 张荣华, 有机化学, 2016, 36, 2121.)
(c) Hao, E. J.; Jiang, X. H.; Fu, D. D.; Wang, D. C.; Xie, M. S.; Qu, G. R.; Guo, H. M. Chin. J. Org. Chem. 2016, 36, 2746(in Chinese). (郝二军, 蒋小涵, 付丹丹, 王东超, 谢明胜, 渠桂荣, 郭海明, 有机化学, 2016, 36, 2746.)
(d) Tian, K.; Meng, J.; Gan, Y. Y.; Li, X. Q.; Wu, S. Q.; Chen, J.; Li, W.; Qi, Y. Y.; Hu, W. N.; Wang, Z. C.; Ouyang G. P. Chin. J. Org. Chem. 2018, 38, 2657(in Chinese). (田坤, 孟娇, 甘宜远, 李小琴, 巫受群, 陈洁, 李文, 漆亚云, 胡伟男, 王贞超, 欧阳贵平, 有机化学, 2018, 38, 2657.)
[7] (a) Tugrak, M.; Inci Gul, H.; Sakagami, H.; Gulcin, I.; Supuran, C. T. Bioorg. Chem. 2018, 81, 433.
(b) Jangra, H.; Chen, Q.; Fuks, E.; Zenz, I.; Mayer, P.; Ofial, A. R.; Zipse, H.; Mayr, H. J. Am. Chem. Soc. 2018, 140, 16758.
(c) Chen, Y. R.; Ganapuram, M. R.; Hsieh, K. H.; Chen, K. H.; Karanam, P.; Vagh, S. S.; Liou, Y. C.; Lin, W. W. Chem. Commun. 2018, 54, 12702.
(d) Xu, H.; Sha, F.; Li, Q.; Wu, X. Y. Org. Biomol. Chem. 2018, 16, 7214.
[8] (a) Wang, X. H.; Yan, C.-G. Synthesis 2014, 46, 1059.
(b) Shi, Y. G.; Wang, X. H.; Liu, R. Z.; C. G. Yan, Chem. Commun. 2016, 52, 6280.
(c) Zhang, Y. Y.; Han, Y.; Sun, J.; Yan, C. G. ChemistrySelect 2017, 2, 7382.
(d) Cao, J.; Sun, J. Yan, C. G. Org. Biomol. Chem. 2018, 16, 4170.
(e) Sun, J.; Zhang, Y.; Shi, R. G.; Yan, C. G. Org. Biomol. Chem. 2019, 17, 3978.
(f) Liu, D.; Sun, J.; Zhang, Y.; Yan, C. G. Org. Biomol. Chem. 2019, 17, 8008.
(g) Yang, W. J.; Fang, H. L.; Sun, J. Yan, C. G. ACS Omega 2019, 4, 13553.
(h) Huang, Y.; Fang, H. L.; Huang, Y. X.; Sun, J.; Yan, C. G. J. Org. Chem. 2019, 84, 1912437.
[9] (a) Kröhnke, F.; Zecher, W. Angew. Chem., Int. Ed. 1962, 1, 626.
(b) Kröhnke, F. Angew. Chem., Int. Ed. 1963, 2, 225.
(c) Jacobs, J.; Van Hende, E.; Claessens, S.; De Kimpe, N. Curr. Org. Chem. 2011, 15, 1340.
(d) Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642.
[10] (a) Constable, E. C.; Edwards, A. J.; Martínez-Máńez, R.; Raithby, P. R. J. Chem. Soc., Dalton Trans. 1995, 3253.
(b) Eryazici, I.; Moorefield, C. N.; Durmus, S.; Newkone, G. R. J. Org. Chem. 2006, 71, 1009.
(c) Tu, S. J.; Jia, R. H.; Jiang, B.; Zhang, J. Y.; Zhang, Y.; Yao, C. S.; Ji, S. J. Tetrahedron 2007, 63, 381.
[11] (a) Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5, 435.
(b) Sasaki, T.; Kanematsu, K.; Yukimoto, Y.; Ochiai, S. J. Org. Chem. 1971, 36, 813.
(c) Xia, Z. Q.; Przewloka, T.; Koya, K.; Ono, M.; Chen, S. J.; Sun, L. J. Tetrahedron Lett. 2006, 47, 8817.
[12] (a) Dinica, R. M.; Druta, I. I.; Pettinari, C. Synlett 2000, 1013.
(b) Furdui, B.; Dinica, R.; Druta, I. I.; Demeunynck, M. Synthesis 2006, 2640.
[13] (a) Zhang, X. C.; Huang, W. Y. Synthesis 1999, 1, 51.
(b) Wu, K.; Chen, Q. Y. Synthesis 2003, 35.
(c) Chuang, C. P.; Tsai, A. I. Synthesis 2006, 675.
[14] (a) Ruano, J. L. G.; Fraile, A.; Martín, M. R.; González, G.; Fajardo, C.; Martín-Castro, A. M. J. Org. Chem. 2011, 76, 3296.
(b) Khlebnikov, A. F.; Golovkina, M. V.; Novikov, M. S.; Yufit, D. S. Org. Lett. 2012, 14, 3768.
(c) Brioche, J.; Meyer, C.; Cossy, J. Org. Lett. 2015, 17, 2800.
[15] (a) Liu, Y.; Sun, J. W. J. Org. Chem. 2012, 77, 1191.
(b) Osyanin, V. A.; Osipov, D. V.; Klimochkin, Y. N. J. Org. Chem. 2013, 78, 5505.
(c) Wang, F. Y.; Shen, Y. M.; Hu, H. Y.; Wang, X. S.; Wu, H.; Liu, Y. J. Org. Chem. 2014, 79, 9556.
[16] (a) Allgäuer, D. S.; Mayer, P.; Mayr, H. J. Am. Chem. Soc. 2013, 135, 15216.
(b) Allgäuer, D. S.; Mayr, H. Eur. J. Org. Chem. 2013, 6379.
(c) Allgäuer, D. S.; Mayr, H. Eur. J. Org. Chem. 2014, 2956.
(d) Hopf, H.; Jones, P. G.; Nicolescu, A.; Bicu, E.; Birsa, L. M.; Belei, D. Chem.-Eur. J. 2014, 20, 5565.
[17] (a) Yan, C. G.; Cai, X. M.; Wang, Q. F.; Wang, T. Y.; Zheng, M. Org. Biomol. Chem. 2007, 5, 945.
(b) Yan, C. G.; Song, X. K.; Wang, Q. F.; Sun, J. Siemeling, U.; Bruhn, C. Chem. Commun. 2008, 1440.
(c) Wang, Q. F.; Song, X. K.; Chen, J.; Yan, C. G. J. Comb. Chem. 2009, 11, 1007.
(d) Wang, Q. F.; Hou, H.; Hui, L.; Yan, C. G. J. Org. Chem. 2009, 74, 7403.
(e) Yan, C. G.; Wang, Q. F.; Song, X. K.; Sun, J. J. Org. Chem. 2009, 74, 710.
(f) Wang, Q. F.; Hui, L.; Hou, H.; Yan, C. G. J. Comb. Chem. 2010, 12, 260.
(g) Han, Y.; Chen, J.; Hui, L.; Yan, C. G. Tetrahedron 2010, 66, 7743.
[18] (a) Hou, H.; Zhang, Y.; Yan, C. G. Chem. Commun. 2012, 48, 4492.
(b) Hui, L.; Li, H. Y.; Yan, C. G. Eur. J. Org. Chem. 2012, 3157.
(c) Wu, L.; Sun, J.; Yan. C. G. Org. Biomol. Chem. 2012, 10, 9452.
(d) Shen, G. L.; Sun, J.; Yan, C. G. Org. Biomol. Chem., 2015, 13, 10929.
(e) Shen, G. L.; Sun, J.; Yan, C. G. RSC Adv. 2015, 5, 4475.
(f) Liu, L. Z.; Wang, X. Y.; Sun, J.; Yan, C. G. Tetrahedron Lett. 2015, 56, 6711.
[19] (a) Banothu, J.; Basavoju, S.; Bavantula, R. J. Heterocycl. Chem. 2015, 52, 853.
(b) Majumder, S.; Sharma, M.; Bhuyan, P. J. Tetrahedron Lett. 2013, 54, 6868.
[20] (a) Shen, G. L.; Sun, J.; Yan, C. G. Chin. J. Chem. 2016, 34, 412.
(b) Liu, R. Z.; Shi, R. G.; Sun, J.; Yan, C. G. Org. Chem. Front. 2017, 4, 354.
(c) Shi, R. G.; Sun, J.; Yan, C. G. ACS Omega 2017, 2, 7820.
[21] (a) Fujita, R.; Hoshino, M.; Tojyo, Y.; Kimura, A.; Hongo, H. Yakugaku Zasshi 2006, 126, 99.
(b) Fujita, R.; Watanabe, N.; Tomisawa, H. Heterocycles 2001, 55, 435.
(c) Fujita, R.; Hoshino, M.; Tomisawa, H. Chem. Pharm. Bull. 2006, 54, 334.
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