Citation: Zhang Pengpeng, Chen Wenwen, Feng Hua, Chen Jianxin. Synthesis of 3-Hydroxy-3-heterocyclebutylamide Derivatives Using Carbamoylsilanes as an Amide Source[J]. Chinese Journal of Organic Chemistry, ;2019, 39(12): 3560-3566. doi: 10.6023/cjoc201906033 shu

Synthesis of 3-Hydroxy-3-heterocyclebutylamide Derivatives Using Carbamoylsilanes as an Amide Source

College of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041004

Corresponding author: Chen Jianxin, jjxxcc2002@yahoo.com
Received Date: 28 June 2019
Revised Date: 22 July 2019
Available Online: 7 December 2019
Fund Project: the Foundation for Returness Overseas Scientists of Shanxi Province 0713Project supported by the Foundation for Returness Overseas Scientists of Shanxi Province (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Natural Science Youth Foundation of Shanxi Province (No. 201701D221033)the Natural Science Foundation of Shanxi Province 2012011046-9the Natural Science Youth Foundation of Shanxi Province 201701D221033

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3-Hydroxy-3-heterocyclebutyl amide derivatives were directly synthesized in 56%~85% yields by nucleophilic addition of various carbamoylsilanes to oxetane-3-one or thietane-3-one in toluene under mild and catalyst-free conditions. This method will provide an efficient route for the synthesis of drugs containing four-membered heterocycles which have not additional stereocentres. The procedure can prepare 3-hydroxy-3-heterocyclebutyl tertiary, secondary and primary amides as well as having a stereocentre connecting with nitrogen atom by selecting different carbamoylsilanes. A comparison of the results obtained from reaction of various carbamoylsilanes indicated that the size of group on the amide group was an important factor in the addition reaction, which influenced on both the reaction time and yields. The reaction has the advantages of mild conditions, less by-products, good yield and simple post-treatment, and is a new method for the efficient preparation of 3-hydroxy-3-heterocycle butylamides.
- carbamoylsilane,
- α-hydroxyamides,
- heterocyclicbutylamides,
- nucleophilic addition,
- synthetic methods
1. [1]
  Bull, J. A.; Croft, R. A.; Davis, O. A.; Doran, R.; Morgan, K. F. Chem. Rev. 2016, 116, 12150. doi: 10.1021/acs.chemrev.6b00274
2. [2]
  Fujishima, T.; Nozaki, T.; Suenga, T. Bioorg. Med. Chem. 2013, 21, 5209. doi: 10.1016/j.bmc.2013.06.032
3. [3]
  Wuitschik, G.; Rogers-Evans, M.; Buckl, A.; Bernasconi, M.; Marki, M.; Godel, T.; Fischer, H.; Wagner, B.; Parrilla, I.; Schuler, F.; Schneider, J.; Alker, A.; Schweizer, W. B.; Muller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4512. doi: 10.1002/anie.200800450
4. [4]
  Burkhard, J. A.; Wuitschik, G.; Rogers-Evans, M.; Muller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 9052. doi: 10.1002/anie.200907155
5. [5]
  Cheong, J. E.; Zaffagni, M.; Chung, I.; Xu, Y.-J.; Wang, Y.-Q.; Jernigan, F. E.; Zetter, B. R.; Sun, L. Eur. J. Med. Chem. 2018, 114, 372.
6. [6]
  Rowland, A. T.; Drawbaugh, R. S.; Dalton, J. R. J. Org. Chem. 1977, 42, 487. doi: 10.1021/jo00423a020
7. [7]
  Martínez-Sáez, N.; Sun, S.; Oldrini, D.; Sormanni, P.; Boutureira, O.; Carboni, F.; Compañón, I.; Deery, M. J.; Vendruscolo, M.; Corzana, F.; Adamo, R.; Bernardes, G. J. L. Angew. Chem., Int. Ed. 2017, 129, 15159. doi: 10.1002/ange.201708847
8. [8]
  Wuitschik, G.; Carreira, E. M.; Wagner, B.; Fischer, H.; Parrilla, I.; Schuler, F.; Rogers-Evans, M.; Muller, K. J. J. Med. Chem. 2010, 53, 3227. doi: 10.1021/jm9018788
9. [9]
  Beadle, J. D.; Knuhtsen, A.; Hoose, A.; Raubo, P.; Jamieson, A. G. Org. Lett. 2017, 19, 3303. doi: 10.1021/acs.orglett.7b01466
10. [10]
  Geden, J. V.; Beasley, B. O.; Clarkson, G. J.; Shipman, M. J. Org. Chem. 2013, 78, 12243. doi: 10.1021/jo4020485
11. [11]
  Dejaegher, Y.; Kuz'menok, N. M.; Zvonok A. M.; Kimpe, N. D. Chem. Rev. 2002, 102, 29. doi: 10.1021/cr990134z
12. [12]
  Mikami, K.; Aikawa, K.; Aida, J. Synlett 2011, 2719.
13. [13]
  Sharma, R.; Williams, L. J. Org. Lett. 2013, 15, 2202. doi: 10.1021/ol400749e
14. [14]
  Kazakova, O. B.; Khusnutdinova, E. F.; Lobov, A. N.; Zvereva, T. I.; Suponitskii, K. Y. Chem. Nat. Compd. 2011, 46, 897. doi: 10.1007/s10600-011-9777-8
15. [15]
  Hamill, R.; Jones, B.; Pask, C. M.; Sridharan, V. Tetrahedron Lett. 2019, 60, 1126. doi: 10.1016/j.tetlet.2019.03.042
16. [16]
  Beasley, B. O.; Clarkson, G. J.; Shipman, M. Tetrahedron Lett. 2012, 53, 2951. doi: 10.1016/j.tetlet.2012.03.065
17. [17]
  Kozikowski, A. P.; Fauq, A. H. Synlett 1991, 783.
18. [18]
  Suenega, T.; Fujishima, T. Tetrahedron 2018, 74, 1461.
19. [19]
  Roesner, S.; Saunders, G. J.; Wilkening, I.; Jayawant, E.; Geden, J. V.; Kerby, P.; Dixon, A. M.; Notman, R.; Shipman, M. Chem. Sci. 2019, 10, 2465. doi: 10.1039/C8SC05474F
20. [20]
  Yao, Y.; Li, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2014, 34, 2124 (in Chinese).
21. [21]
  Yao, Y.; Li, W.-T.; Tong, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2015, 35, 223 (in Chinese).
22. [22]
  Chen, X.-J.; Chen, J.-X. Mendeleev Commun. 2013, 23, 106. doi: 10.1016/j.mencom.2013.03.019
23. [23]
  Li, W.-D.; Han, S.-H.; Liu, Y.-H.; Chen, J.-X. Chin. J. Org. Chem. 2017, 37, 2423 (in Chinese).
24. [24]
  Zhang, W.-J.; Cao, P.; Guo, Q.-L.; Chen, J.-X. Curr. Org. Synth. 2017, 14, 1067.
25. [25]
  Ma, F.; Liu, H.; Chen, J.-X. Tetrahedron Lett. 2016, 57, 5246. doi: 10.1016/j.tetlet.2016.10.040
26. [26]
  Han, Y.-L.; Tong, W.-T.; Liu, H.; Chen, J.-X. Chin. J. Org. Chem. 2018, 38, 1993 (in Chinese).
27. [27]
  Tong, W.-T.; Cao, P.; Liu, Y.-H. J. Org. Chem. 2017, 82, 11603. doi: 10.1021/acs.joc.7b01028
28. [28]
  Soeta, T.; Kojima, Y.; Ukaji, Y.; Inomata, K. Org. Lett. 2010, 12, 4341. doi: 10.1021/ol101763w
29. [29]
  Wang, Y.-K.; Yin, H.; Tang, X.-F.; Wu, Y.-F.; Meng, Q.-W.; Gao, Z.-X. J. Org. Chem. 2016, 81, 7042. doi: 10.1021/acs.joc.6b00856
30. [30]
  Zhang P.-P.; Han, S.-H.; Chen, J.-X. Mendeleev Commun. 2019, 29, 326. doi: 10.1016/j.mencom.2019.05.029
31. [31]
32. [32]
  Reeves, J. T.; Lorenc, C.; Camara, K.; Li, Z.-B.; Lee, H. W.; Busacca, C. A.; Senanayake, C. H. J. Org. Chem. 2014, 79, 5895. doi: 10.1021/jo500848a
33. [33]
  Reeves, J. T.; Tan, Z.-L.; Herbage, M. A.; Han, Z. S.; Marsini, M. A.; Li, Z.-B.; Li, G.-S.; Xu, Y.-B.; Fandrick, K. R.; Gonnella, N. C.; Campbell, S.; Ma, S.-L.; Grinberg, N.; Lee, H. W.; Lu, B. Z.; Senanayake, C. H. J. Am. Chem. Soc. 2013, 135, 5565. doi: 10.1021/ja402647m
34. [34]
  Schollkopf, U.; Beckhaus, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 293. doi: 10.1002/anie.197602931
35. [35]
  Lang, Q.-W.; Hu, X.-N.; Huang, P.-Q. Sci. China Chem. 2016, 59, 1638. doi: 10.1007/s11426-016-0224-5
36. [36]
  Stopka, T.; Adler, P.; Hagu, G.; Zhang, H.-Q.; Tona, V.; Maulide, N. Synthesis 2019, 51, 194. doi: 10.1055/s-0037-1610411
37. [37]
  Huang, P.-Q. Acta Chim. Sinica 2018, 76, 357 (in Chinese).
38. [38]
  Davies, S. G.; Ichihara, O. Tetrahedron Lett. 1998, 39, 6045. doi: 10.1016/S0040-4039(98)01193-9
39. [39]
  Cunico, R. F.; Motta, A. R. Org. Lett. 2005, 7, 771. doi: 10.1021/ol040066p
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