SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 1: 223 - 227

DOI: https://doi.org/10.6023/cjoc201408006

Notes

Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes

  • Yao Yuan ,
  • Li Weidong ,
  • Tong Wenting ,
  • Chen Jianxin
Expand
  • a College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004;
    b The First Experimental Middle School of Linfen City, Linfen 041000

Received date: 2014-06-23

  Revised date: 2014-09-10

  Online published: 2014-09-25

Supported by

Project supported by the Shanxi Province Foundation for Returness Overseas Scientists of China (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of Shanxi Normal University (No. SD2014CXXM-53).

Fold

Abstract

α-Hydroxyamides are directly synthesized by the reaction of N,N-dimethylcarbamoyl(trimethyl)silane with various aldehydes. Most of yields are 71%～91%. Their structures were confirmed by 1H NMR, 13C NMR, IR and elemental analysis. Through carbamoylsilane reacted with the variety of aldehydes, the results indicated that the electronic effect was an important factor in the addition reaction, which influenced on the rate and yields of the reaction. A reaction mechanism is proposed. The main advantages of the developed methodology are mild reaction conditions, less byproducts, high yields of products and simple work-up procedure. An effective synthesis method of α-hydroxyamides has been developed.

Key words： nucleophilic addition; carbamoylsilane; α-hydroxyamides; aldehydes; carbenes

Cite this article

Yao Yuan , Li Weidong , Tong Wenting , Chen Jianxin . Synthesis of α-Hydroxyamides from a Carbamoylsilane and Aldehydes[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 223 -227 . DOI: 10.6023/cjoc201408006

References

[1] Chen, J.-X.; Cunico, R. F. Tetrahedron Lett. 2002, 43, 8595.
[2] Chen, J.-X.; Cunico, R. F. Tetrahedron Lett. 2003, 44, 8025.
[3] Chen, J.-X.; Pandey, R. K.; Cunico, R. F. Tetrahedron: Asymmmetry 2005, 16, 941.
[4] Cunico, R. F.; Rajesh, K. P.; Chen, J.-X.; Adalie, R. M. Synlett 2005, 3157.
[5] Chen, J.-X.; Cunico, R. F. J. Org. Chem. 2004, 69, 5509.
[6] Chen X.-J.; Chen, J.-X. Mendeleev Commun. 2013, 23, 106.
[7] Ma, F.; Chen, J.-X. Acta Chim. Sinica 2013, 71, 1118 (in Chinese). (马菲, 陈建新, 化学学报, 2013, 71, 1118.)
[8] Cunico, R. F.; Maity, B. C. Org. Lett. 2002, 4, 4357.
[9] Cunico, R. F.; Maity, B. C. Org. Lett. 2003, 5, 4947.
[10] Cunico, R. F.; Pandey, R. K. J. Org. Chem. 2005, 70, 5344.
[11] Cunico, R. F.; Pandey, R. K. J. Org. Chem. 2005, 70, 9048.
[12] Cunico, R. F. Tetrahedron Lett. 2002, 43, 355.
[13] Schollkopf, U.; Beckhaus, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 293.
[14] Merino, O.; Santoyo, B. M.; Montiel, L. E.; Jiménez-Vázquez, H. A.; Zepeda, L. G.; Tamariz, J. Tetrahedron Lett. 2010, 51, 3738.
[15] Shteinberg, L. Y. Russ. J. Appl. Chem. 2009, 82, 619.
[16] Kuduk, S. D.; Chang, R. K.; Dipardo, R. M.; Di Marco, C. N.; Murphy, K. L.; Ransom, R. W.; Reiss, D. R.; Tang, C.; Prueksari- tanont, T.; Pettibone, D. J.; Boch, M. G. Bioorg. Med. Chem. Lett. 2008, 18, 5107.
[17] Soeta, T.; Kojima, Y.; Ukaji, Y.; Inomata, K. Tetrahedron Lett. 2011, 52, 2557.
[18] Ramon, D. J.; Yus, M. Tetrahedron Lett. 1993, 34, 7115.
[19] Nudelman, N. S.; Linares, G. E. G. J. Org. Chem. 2000, 65, 1629.
[20] Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
[21] Domling, A.; Ugi, L. Angew. Chem., Int. Ed. 2000, 39, 3168.
[22] Yue, T.; Wang, M.-X.; Wang, D.-X.; Masson, G.; Zhu, J. Angew. Chem., Int. Ed. 2009, 48, 6717.
[23] Mihara, H.; Xu, Y.; Shepherd, N. E.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 8384.
[24] Cunico, R. F.; Chen, J.-X. Synth. Commun. 2003, 33, 1963.
[25] Cunico, R. F. Tetrahedron Lett. 2001, 42, 2931.
[26] Cunico, R. F.; Motta, A. R. Org. Lett. 2005, 7, 771.

Options
Outlines

/

〈 〉