Synthesis 2019; 51(11): 2402-2408
DOI: 10.1055/s-0037-1612279
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Three-Component Synthesis of Pyrrolidin-2-ones via a Sequential Wittig/Nucleophilic Addition/Cyclization Reaction

Zhi-Rong Guan ‡
,
Shuai Liu ‡
,
Zi-Ming Liu
,
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, P. R. of China   eMail: mwding@mail.ccnu.edu.cn
› Institutsangaben
We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (No. 21572075) and the 111 Project B17019.
Weitere Informationen

Publikationsverlauf

Received: 06. November 2018

Accepted after revision: 28. Januar 2019

Publikationsdatum:
04. März 2019 (online)

‡ These authors contributed equally to this work.

Abstract

A new efficient synthesis of pyrrolidin-2-ones via sequential Wittig reaction/nucleophilic addition/cyclization was developed. The Wittig reaction of the phosphoranes with isocyanates produced ketenimine intermediates that were then treated with primary amines to give amidines, which were treated with catalytic sodium alkoxide to give 2-imino-5-oxopyrrolidine-3-carboxylates in good yields.

Supporting Information

 
  • References

  • 1 Muralidharan VP, Alagumuthu M, Iyer SK. Bioorg. Med. Chem. Lett. 2017; 27: 2510
  • 2 Koszytkowska-Stawińska M, Kołaczkowska E, Adamkiewicz E, De Clercq E. Tetrahedron 2007; 63: 10587
  • 3 Wang T, Dong S, Chen X, Qian K, Wang H, Quan H, Zhang Z, Zuo Y, Huang L, Li D, Yang M, Yang S, Jin Y, Wang Z. Bioorg. Med. Chem. Lett. 2018; 28: 1324
  • 4 Han J.-J, Bao L, He L.-W, Zhang X.-Q, Yang X.-L, Li S.-J, Yao Y.-J, Liu H.-W. J. Nat. Prod. 2013; 76: 1448
  • 5 Aida J, Fushimi M, Kusumoto T, Sugiyama H, Arimura N, Ikeda S, Sasaki M, Sogabe S, Aoyama K, Koike T. J. Med. Chem. 2018; 61: 9205
  • 6 Zaręba P, Dudek M, Lustyk K, Siwek A, Starowicz G, Bednarski M, Nowiński L, Raźny K, Sapa J, Malawska B, Kulig K. Bioorg. Med. Chem. 2015; 23: 2104
  • 7 Sifferlen T, Boller A, Chardonneau A, Cottreel E, Gatfield J, Treiber A, Roch C, Jenck F, Aissaoui H, Williams JT, Brotschi C, Heidmann B, Siegrist R, Boss C. Bioorg. Med. Chem. Lett. 2015; 25: 1884
  • 8 Hu M, Guo L.-Y, Han Y, Tan F.-L, Song R.-J, Li J.-H. Chem. Commun. 2017; 53: 6081
  • 9 Pan G.-H, Ouyang X.-H, Hu M, Xie Y.-X, Li J.-H. Adv. Synth. Catal. 2017; 359: 2564
  • 10 Dawange M, Parekh N, Kumbhar A, Dehaen W, Kusurkar R. New J. Chem. 2017; 41: 3612
  • 11 Hashmi AS. K, Yang W, Yu Y, Hansmann MM, Rudolph M, Rominger F. Angew. Chem. Int. Ed. 2013; 52: 1329
  • 12 Anderson JC, Horsfall LR, Kalogirou AS, Mills MR, Stepney GJ, Tizzard GJ. J. Org. Chem. 2012; 77: 6186
  • 13 Pelletier SM.-C, Ray PC, Dixon DJ. Org. Lett. 2009; 11: 4512
  • 14 Arfaoui A, Saadi F, Smida YB, Arfaoui Y, Nefzi A, Amri H. Tetrahedron Lett. 2015; 56: 98
  • 15 Xie C, Han D, Hu Y, Liu J, Xie T. Tetrahedron Lett. 2010; 51: 5238
  • 16 Koch A, Kumar S, Ravikanth M. Tetrahedron 2017; 73: 1459
  • 17 Mandal D, Gupta R, Young RD. J. Am. Chem. Soc. 2018; 140: 10682
  • 18 Schultze C, Schmidt B. J. Org. Chem. 2018; 83: 5210
  • 19 Lorton C, Voituriez A. J. Org. Chem. 2018; 83: 5801
  • 20 Volvoikar PS, Tilve SG. Tetrahedron Lett. 2018; 59: 1851
  • 21 Begala M, Caboni P, Matos MJ, Delogu GL. Tetrahedron Lett. 2018; 59: 1711
    • 22a Krow GR. Angew. Chem., Int. Ed. Engl. 1971; 10: 435
    • 22b Nallagangula M, Namitharan K. Org. Lett. 2017; 19: 3536
    • 22c Anugu RR, Chegondi R. J. Org. Chem. 2017; 82: 6786
    • 22d Ning Y, Otani Y, Ohwada T. J. Org. Chem. 2017; 82: 6313
    • 22e Arora I, Shaw AK. Tetrahedron 2016; 72: 5479
    • 23a Ren ZL, Guan ZR, Kong HH, Ding MW. Org. Chem. Front. 2017; 4: 2044
    • 23b Ren ZL, Sun M, Guan ZR, Ding MW. Synlett 2018; 29: 106
    • 23c Yan YM, Rao Y, Ding MW. J. Org. Chem. 2017; 82: 2772
    • 23d Wang L, Sun M, Ding MW. Eur. J. Org. Chem. 2017; 2568
    • 23e Wang L, Guan ZR, Ding MW. Org. Biomol. Chem. 2016; 14: 2413
  • 24 Eyjólfsson R. Acta Chem. Scand. 1970; 24: 3075