Citation: Shi Wangyu, Xu Jiaqing, Mao Biming, Jia Hao, Huang Jiaxing, Guo Hongchao. [3+2] Cycloaddition of Methylenedihydrobenzofurandiones and Nitrilimines: Synthesis of Sipropyrazole Compounds[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 756-762. doi: 10.6023/cjoc201907030 shu

[3+2] Cycloaddition of Methylenedihydrobenzofurandiones and Nitrilimines: Synthesis of Sipropyrazole Compounds

Department of Chemistry, College of Science, China Agricultural University, Beijing 100193

Corresponding author: Huang Jiaxing, hchguo@cau.edu.cn Guo Hongchao, 05084@cau.edu.cn
Received Date: 22 July 2019
Revised Date: 18 October 2019
Available Online: 1 November 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21572264)Project supported by the National Natural Science Foundation of China No.21572264

Figures(2)

The[3+2] cycloaddition of methylenedihydrobenzofurandiones and nitrilimines worked efficiently in CHCl₃ at room temperature in the presence of Et₃N, producing biologically interesting spirocyclic pyrazole derivatives in high yield (78%~94%) with excellent diastereoselectivity.
- cycloaddition,
- nitrilimine,
- spirocyclic compound,
- pyrazole
1. [1]
2. [2]
  Ivachtchenko A. V., Ivanenkov Y. A., Mitkin O. D., Vorobiev A. A., Kuznetsova I. V., Shevkun N. A., Koryakova A. G., Karapetian R. N., Trifelenkov A. S., Kravchenko D. V., Veselov M. S., Chufarova N. V.Eur. J. Med. Chem., 2015, 99:51. doi: 10.1016/j.ejmech.2015.05.039
3. [3]
  Merino-Montiel P., López O., lvarez E., Fernández-Bola osa J. G.Tetrahedron, 2012, 68:4888. doi: 10.1016/j.tet.2012.03.087
4. [4]
  Gasch C., Merino-Montiel P., López O., Fernández-Bola osa J. G., Fuentes J.Tetrahedron, 2010, 66:9964. doi: 10.1016/j.tet.2010.09.109
5. [5]
  Kamal A., Reddy B. V. S., Sridevi B., Ravikumar A., Venkateswarlu A., Sravanthi G., Sridevi J. P., Yogeeswari P., Sriram D.Bioorg. Med. Chem. Lett., 2015, 25:3867. doi: 10.1016/j.bmcl.2015.07.057
6. [6]
  Huisgen R., Fleischmann R., Eckell A.Tetrahedron Lett., 1960, 12:5.
7. [7]
  Belletire J. L., Hagedom C. E., Ho D. M., Krause J.Tetrahedron Lett., 1993, 34, 797. doi: 10.1016/0040-4039(93)89015-I
8. [8]
  Mei L. Y., Tang X. Y., Shi M.Chem.-Eur. J., 2014, 20:1. doi: 10.1002/chem.201390210
9. [9]
  Hashimoto T., Maruoka K.Chem. Rev., 2015, 115:5366. doi: 10.1021/cr5007182
10. [10]
  (a) Gothelf K. V., J rgensen K. A.Chem. Rev., 1998, 98: 863. (b) Lima C. G. S., Ali A., Berkel S. S. V., Westermann B., Paix o M. W.Chem. Commun., 2015, 51: 10784. (c) Narayan R., Potowski M., Jia Z., Antonchick A. P., Waldmann H.Acc. Chem. Res., 2014, 47: 1296. (d) Fustero S., Rosell M. S., Barrio P., Fuentes A. S.Chem. Rev., 2011, 111: 6984. (e) Fanga X., Wang C. J.Org. Biomol. Chem., 2018, 16: 2591.
11. [11]
12. [12]
  Huisgen R., Grashey R., Seidel M., Wallbilllich G., Knupfer H., Schmidt R. Justus Liebigs Ann. Chem., 1962, 653:105. doi: 10.1002/jlac.19626530113
13. [13]
  Tsuge O., Watanabe H., Kiryu Y.Bull. Chem. Soc. Jpn., 1979, 52:3654. doi: 10.1246/bcsj.52.3654
14. [14]
  Gandolfi R., Toma L.Tetrahedron, 1979, 36:935.
15. [15]
  (a) Guo Z., Jia H., Liu H., Wang Q., Huang J., Guo H.Org. Lett., 2018, 20: 2939. (b) Long W., Chen S., Zhang X., Fang L., Wang Z.Tetrahedron, 2018, 74: 6155.
16. [16]
  Wang B., Wang Q. J., Liu H. L., Liao J. N., Huang J. X., Guo H.Chin. J. Org. Chem., 2019, 39:1354(in Chinese).
17. [17]
  (a) Na R., Jing C., Xu Q., Jiang H., Wu X., Shi Y., Zhong J., Wang M., Benitez D., Tkatchouk E., Goddard Ⅲ W. A., Guo H., Kwon O.J. Am. Chem. Soc., 2011, 133: 13337. (b) Wu X., Na R., Liu H., Liu J., Wang M., Zhong J., Guo H.Tetrahedron Lett., 2012, 53: 342. (c) Guo H., Liu H., Zhu F.-L., Na R., Jiang H., Wu Y., Zhang L., Li Z., Yu H., Wang B., Xiao Y., Hu X.-P., Wang M.Angew. Chem., Int. Ed., 2013, 52: 12641. (d) Zhang L., Yu H., Yang Z., Liu H., Li Z., Guo J., Xiao Y., Guo H.Org. Biomol. Chem., 2013, 11: 8235. (e) Liu H., Wu Y., Zhao Y., Li Z., Zhang L., Yang W., Jiang H., Jing C., Yu H., Wang B., Xiao Y., Guo H.J. Am. Chem. Soc., 2014, 136: 2625. (f) Zhang L., Liu H., Qiao G., Hou Z., Liu Y., Xiao Y., Guo H.J. Am. Chem. Soc., 2015, 137: 4316. (g) Liu H., Yuan C., Wu Y., Xiao Y., Guo H.Org. Lett., 2015, 17: 4220. (h) Gao Z., Wang C., Yuan C., Zhou L., Xiao Y., Guo H.Chem. Commun., 2015, 51: 12653. (i) Yang W., Zhang Y., Qiu S., Zhao C., Zhang L., Liu H., Zhou L., Xiao Y., Guo H.RSC Adv., 2015, 5: 62343. (j) Liu Y., Yang W., Wu Y., Mao B., Gao X., Liu H., Sun Z., Xiao Y., Guo H.Adv. Synth. Catal., 2016, 358: 2867. (k) Wang C., Gao Z., Zhou L., Yuan C., Sun Z., Xiao Y., Guo H.Org. Lett., 2016, 18: 3418. (l) Yuan C., Zhou L., Xia M., Sun Z., Wang D., Guo H.Org. Lett., 2016, 18: 5644. (m) Li Z., Yu H., Liu Y., Zhou L., Sun Z., Guo H.Adv. Synth. Catal., 2016, 358: 1880. (n) Wang C., Jia H., Zhang C., Gao Z., Zhou L., Yuan C., Xiao Y., Guo H.J. Org. Chem., 2017, 82: 633. (o) Yang W., Sun W., Zhang C., Wang Q., Guo Z., Mao B., Liao J., Guo H.ACS Catal., 2017, 7: 3142. (p) Zhou L., Yuan C., Zhang C., Zhang L., Gao Z., Wang C., Liu H., Wu Y., Guo H.Adv. Synth. Catal., 2017, 359: 2316. (q) Wang B., Liu H., Wang Q., Yuan C., Jia H., Liu C., Guo H.Tetrahedron, 2017, 73: 5926. (r) Liu H., Zhao Y., Li Z., Jia H., Zhang C., Xiao Y., Guo H.RSC Adv., 2017, 7: 29515. (s) Gao Z., Wang C., Zhou L., Yuan C., Xiao Y., Guo H.Org. Lett., 2018, 20, 4302. (t) Zhou L., Yuan C., Zeng Y., Liu H., Wang C., Gao X., Wang Q., Zhang C., Guo H.Chem. Sci., 2018, 9: 1831. (u) Yuan C., Wu Y., Wang D., Zhang Z., Wang C., Zhou L., Zhang C., Song B., Guo H.Adv. Synth. Catal., 2018, 360: 652. (v) Jia H., Guo Z., Liu H., Mao B., Shi X., Guo H.Chem. Commun., 2018, 54: 7050.
18. [18]
  Takizawa S., Nguyen T. M. N., Grossmann A., Enders D., Sasai H.Angew. Chem., Int. Ed., 2012, 51:5423. doi: 10.1002/anie.201201542
19. [19]
  Liu H. L., Jia H., Wang, B; Xiao Y., Guo; H. Org. Lett., 2017, 19:4714. doi: 10.1021/acs.orglett.7b01961
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