Chinese Journal of Organic Chemistry >
Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source
Received date: 2018-03-30
Revised date: 2018-05-13
Online published: 2018-05-24
Supported by
Project supported by the Shanxi Provincal Foundation for Returness Overseas Scientists (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of the Modern College of Arts and Science, Shanxi Normal University (No. WL2016CXCY-YJ-30).
α-(N-Sulfonyl)amino amide derivatives are directly synthesized in 71%~89% yields by the reaction of carbamoylsilanes with various N-sulfonylimines in benzene under catalyst-free conditions. The procedure can prepare both tertiary and secondary α-amino amides. A comparison of the results obtained from the N-sulfonylimines containing the variety of alkyl, aryl and heterocyclic ring indicated that the electronic effect was an important factor in the addition reaction, which influenced on the rate and yields of the reaction. The new method is simple and mild procedure, no catalysts conditions, less byproducts and good yields for the preparation of α-aminoamides.
Han Yuling , Tong Wenting , Liu Hui , Chen Jianxin . Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source[J]. Chinese Journal of Organic Chemistry, 2018 , 38(8) : 1993 -2001 . DOI: 10.6023/cjoc201803054
[1] Amstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
[2] Katritzky, A. R.; Kirichenko, N.; Rogovoy, B. V.; He, H.-Y. J. Org. Chem. 2003, 68, 9088.
[3] Najera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584.
[4] Chatel-Chaix, L.; Germain, M. A.; Gotte, M.; Lamarre, D. Curr. Opin. Virol. 2012, 2, 588.
[5] Sanchez, L. M.; Lopez, D.; Vesely, B. A.; Togna, G. D.; Gerwick, W. H.; Kyle, D. E.; Linington, R. G. J. Med. Chem. 2010, 53, 4187.
[6] Erb, W.; Neuville, L.; Zhu, J. P. J. Org. Chem. 2009, 74, 3109.
[7] Lin, Y. S.; Alper, H. Angew. Chem., Int. Ed. Engl. 2001, 40, 779.
[8] Ugi, I.; Steinbruckner, C. Angew. Chem. 1960, 72, 267.
[9] Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
[10] Domling, A. Chem. Rev. 2006, 106, 17.
[11] Pick, R.; Bauer, M.; Kazmaier, U.; Hebach, C. Synlett 2005, 757.
[12] Basso, A.; Banfi, L.; Riva, R.; Guanti, G. J. Org. Chem. 2005, 70, 575.
[13] Rueping, M.; Vila, C. Org. Lett. 2013, 15, 2092.
[14] Mita, T.; Sugawara, M.; Saito, K.; Sato, Y. Org. Lett. 2014, 16, 3028.
[15] Reeves, J. T.; Tan, Z.; 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.; Lu, B.-Z.; Senanayake, C. H. J. Am. Chem. Soc. 2013, 135, 5565.
[16] Li, F.; Zhou, W.; Zheng, L.-S.; Li, L.; Zheng, Z.-J.; Xu, L.-W. Synth. Commun. 2014, 44, 2861.
[17] Dong, C.; Song, T.; Bei, X.-F.; Cui, Y.-M.; Xu, Z.; Xu, L.-W. Catal. Sci. Technol. 2015, 5, 4755.
[18] Xing, P.; Zang, W.; Huang, Z.-G.; Zhan, Y.-X.; Zhu, C.-J.; Jing, B. Synlett 2012, 2269.
[19] Wei, Y.-L.; Huang, W.-S.; Cui, Y.-M.; Yang, K.-F.; Xu, Z.; Xu, L.-W. RSC Adv. 2015, 5, 3098.
[20] Yao, Y.; Li, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2014, 34, 2124(in Chinese). (姚远, 李伟东, 陈建新, 有机化学, 2014, 34, 2124.)
[21] Yao, Y.; Li, W.-T.; Tong, W.-T.; Chen, J.-X. Chin. J. Org. Chem. 2015, 35, 223(in Chinese). (姚远, 李伟东, 仝文婷, 陈建新, 有机化学, 2015, 35, 223.)
[22] Chen, X.-J.; Chen, J.-X. Mendeleev Commun. 2013, 23, 106.
[23] Li, W.-D.; Han, S.-H.; Liu, Y.-H.; Chen, J.-X. Chin. J. Org. Chem. 2017, 37, 2423(in Chinese). (李伟东, 韩生华, 刘艳红, 陈建新, 有机化学, 2017, 37, 2423.)
[24] Wen, X.-P.; Han, Y.-L.; Chen, J.-X. RSC Adv. 2017, 7, 45107.
[25] Tong, W.-T.; Cao, P.; Liu, Y.-H.; Chen, J.-X. J. Org. Chem. 2017, 82, 11603.
[26] Zhang, W. J.; Han, S.-H.; Chen, J.-X. Synth. Commun. 2017, 47, 704.
[27] Ma, F.; Liu, H.; Chen, J.-X. Tetrahedron Lett. 2016, 57, 5246.
[28] Chen, J.-X.; Cunico, R. F. Tetrahedron Lett. 2002, 43, 8595.
[29] Chen, J.-X.; Cunico, R. F. Tetrahedron Lett. 2003, 44, 8025.
[30] Guo, Q.-L.; Wen, X.-P.; Chen, J.-X. Tetrahedron 2016, 72, 8117.
[31] Tong, W.-T.; Liu, H.; Chen, J.-X. Tetrahedron Lett. 2015, 56, 1335.
[32] Hasan, P.; Aneja, B.; Masood, M. M.; Ahmad, M. B.; Yadava, U. Daniliuc, C. G.; Abid, M. RSC Adv. 2017, 7, 11367.
[33] Lin, J.-P.; Long, Y.-Q. Chem. Commun. 2013, 49, 5313.
[34] Lang, Q.-W.; Hu, X.-N.; Huang, P.-Q. Sci. China, Chem. 2016, 59, 1638.
[35] Zheng, J.-F.; Qian, X.-Y.; Huang, P.-Q. Org. Chem. Front. 2015, 2, 927.
[36] Ram, R. N.; Kham, A. A. Synth. Commun. 2001, 31, 841.
[37] Lee, K.-Y.; Lee, C.-G.; Kim, J. N. Tetrahedron Lett. 2003, 44, 1231.
[38] Carbamoylsilane were prepared as reported, see:Cunico, R. F.; Chen, J.-X. Synth. Commun. 2003, 33, 1963.
[39] Schollkopf, U.; Beckhaus, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 293.
[40] Zhang, W.-J.; Cao, P.; Guo, Q.-L.; Chen, J.-X. Curr. Org. Synth. 2017, 14, 1067.
[41] Cunico, R. F.; Motta, A. R. Org. Lett. 2005, 7, 771.
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