Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Copyright (c) 2014 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Zn(OAc)2·2H2O-Catalyzed One-Pot Efficient Synthesis of a-Amino Nitriles

https://doi.org/10.14233/ajchem.2014.17180
V. Venkata Rami Reddy
Centre for Chemical Sciences and Technology, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad-500 085, India
B. Saritha
Department of Chemistry, Vidyajyothi Institute of Technology, Aziznagar Gate C.B Post, Ranga Reddy-500 075, India
R. Ramu
R&D Division, SRC Laboratories Private Limited, Prashant Nagar, Kukatpally, Hyderabad-500 037, India
Ravi Varala
Department of Chemistry, AP-IIIT Basara, Rajiv Gandhi University of Knowledge Technologies, Adilabad-504 107, India
A. Jayashree
Centre for Chemical Sciences and Technology, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : Ravi Varala

ravivarala@rgukt.in

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21

Abstract

A mild, efficient one-pot three component strecker reaction involving electronically and structurally divergent aldehydes, amines and trimethly silyl cyanide in chloroform as solvent at room temperature was accomplished in moderate to excellent yields using an inexpensive and readily available catalyst, Zn(OAc)2.2H2O.

Keywords

Strecker reaction a-Amino nitriles Zn(OAc)2.2H2O Multicomponent reaction
Venkata Rami Reddy, V., Saritha, B., Ramu, R., Varala, R., & Jayashree, A. (2014). Zn(OAc)2·2H2O-Catalyzed One-Pot Efficient Synthesis of a-Amino Nitriles. Asian Journal of Chemistry, 26(21), 7439–7442. https://doi.org/10.14233/ajchem.2014.17180
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. (a) Y.M. Shafran, V.A. Bakulev and V.S. Mokrushin, Russ. Chem. Rev., 58, 148 (1989); doi:10.1070/RC1989v058n02ABEH003432; (b) A. Strecker, Ann. Chem. Pharm., 75, 27 (1850); doi:10.1002/jlac.18500750103; (c) R.O. Duthaler, Tetrahedron, 50, 1539 (1994); doi:10.1016/S0040-4020(01)80840-1; (d) R.M. Williams and J.A. Hendrix, Chem. Rev., 92, 889 (1992); doi:10.1021/cr00013a007.
  2. L.M. Weinstock, P. Davis, B. Handelsman and R. Tull, J. Org. Chem., 32, 2823 (1967); doi:10.1021/jo01284a040.
  3. W.L. Matier, D.A. Owens, W.T. Comer, D. Deitchman, H.C. Ferguson, R.J. Seidehamel and J.R. Young, J. Med. Chem., 16, 901 (1973); doi:10.1021/jm00266a008.
  4. C. Schultz, H. Groger, C. Dinkel, K. Drauz and H. Waldmann, in eds,: B. Cornils and W. A. Herrmann, In Applied Homogeneous Catalysis with Organometallic Compounds, VCH Wiley: Weinheim, edn. 2, Vol. 2, Chapter 3.2.1 (2002).
  5. (a) G.R. Heintzelman, I.R. Meigh, Y.R. Mahajan and S.M. Weinreb, Org. React., 65, 141 (2005); (b) J.E. Tarver Jr., K.M. Terranova and M. Joullie´, Tetrahedron, 60, 10277 (2004); doi:10.1016/j.tet.2004.08.089.; (c) I.A. Motorina, F.W. Fowler and D.S. Grierson, J. Org. Chem., 62, 2098 (1997); doi:10.1021/jo9614046.; (d) N.J. Sisti, I.A. Motorina, M.-E. Tran Huu Dau, C. Riche, F.W. Fowler and D.S. Grierson, J. Org. Chem., 61, 3715 (1996); doi:10.1021/jo9520607.
  6. (a) K.M. Maloney and R.L. Danheiser, Org. Lett., 7, 3115 (2005); doi:10.1021/ol051185n; (b) D.T. Amos, A.R. Renslo and R.L. Danheiser, J. Am. Chem. Soc., 125, 4970 (2003); doi:10.1021/ja034629o; (c) W.J. Middleton and C.G. Krepsan, J. Org. Chem., 33, 3625 (1968); doi:10.1021/jo01273a059.
  7. S.K. De and R.A. Gibbs, Tetrahedron Lett., 45, 7407 (2004); doi:10.1016/j.tetlet.2004.08.071.
  8. M. North, Angew. Chem. Int. Ed., 43, 4126 (2004); doi:10.1002/anie.200301750.
  9. S.I. Murahashi, N. Komiya, H. Terai and T. Nakae, J. Am. Chem. Soc., 125, 15312 (2003); doi:10.1021/ja0390303.
  10. S. Paraskar and A. Sudalai, Tetrahedron Lett., 47, 5759 (2006); doi:10.1016/j.tetlet.2006.06.008.
  11. N.-U.H. Khan, S. Agrawal, R.I. Kureshy, S.H.R. Abdi, S. Singh, E. Suresh and R.V. Jasra, Tetrahedron Lett., 49, 640 (2008); doi:10.1016/j.tetlet.2007.11.136.
  12. M. Narasimhulu, T.S. Reddy, K.C. Mahesh, S.M. Reddy, A.V. Reddy and Y. Venkateswarlu, J. Mol. Catal. Chem., 264, 288 (2007); doi:10.1016/j.molcata.2006.09.036.
  13. L. Royer, S.K. De and R.A. Gibbs, Tetrahedron Lett., 46, 4595 (2005); doi:10.1016/j.tetlet.2005.05.005.
  14. J.S. Yadav, B.V.S. Reddy, B. Eeshwaraiah and M. Srinivas, Tetrahedron, 60, 1767 (2004); doi:10.1016/j.tet.2003.12.043.
  15. B.M. Fetterly, N.K. Jana and J.G. Verkade, Tetrahedron, 62, 440 (2006); doi:10.1016/j.tet.2005.09.117.
  16. A. Heydari, A. Arefi, S. Khaksar and R.K. Shiroodi, J. Mol. Catal. Chem., 271, 142 (2007); doi:10.1016/j.molcata.2007.02.046.
  17. A. Heydari, P. Fatemi and A.-A. Alizadeh, Tetrahedron Lett., 39, 3049 (1998); doi:10.1016/S0040-4039(98)00354-2.
  18. J. Jarusiewicz, Y. Choe, K.S. Yoo, C.P. Park and K.W. Jung, J. Org. Chem., 74, 2873 (2009); doi:10.1021/jo900163w.
  19. S. Kobayashi and H. Ishitani, Chem. Rev., 99, 1069 (1999); doi:10.1021/cr980414z.
  20. (a) H. Groger, Chem. Rev., 103, 2795 (2003); doi:10.1021/cr020038p; (b) C. Spino, Angew. Chem. Int. Ed., 43, 1764 (2004); doi:10.1002/anie.200301686.
  21. B.A.B. Prasad, A. Bisai and V.K. Singh, Tetrahedron Lett., 45, 9565 (2004); doi:10.1016/j.tetlet.2004.11.015.
  22. S. Harusawa, Y. Hamada and T. Shioiri, Tetrahedron Lett., 20, 4663 (1979); doi:10.1016/S0040-4039(01)86677-6.
  23. P. Vachal and E.N. Jacobsen, J. Am. Chem. Soc., 124, 10012 (2002); doi:10.1021/ja027246j.
  24. S. Nakamura, N. Sato, M. Sugimoto and T. Toru, Tetrahedron Asymm., 15, 1513 (2004); doi:10.1016/j.tetasy.2004.03.040.
  25. S. Kobayashi, T. Busujima and S. Nagayama, Chem. Commun., 981 (1998); doi:10.1039/a801464g.
  26. B.C. Ranu, S.S. Dey and A. Hajra, Tetrahedron, 58, 2529 (2002); doi:10.1016/S0040-4020(02)00132-1.
  27. E. Ramu, R. Varala, N. Sreelatha and S.R. Adapa, Tetrahedron Lett., 48, 7184 (2007); doi:10.1016/j.tetlet.2007.07.196.
  28. (a) V.R. Narayana, Z. Pudukulathan and R. Varala, Org. Commun., 6, 110 (2013); (b) A. Kasa, R. Varala, P.M. Swami and P.K. Zubaidha, Chemistry J., 3, 66 (2013); (c) P.S. Kulkarni, D.D. Kondhare, R. Varala and P.K. Zubaidha, J. Serb. Chem. Soc., 78, 909 (2013); doi:10.2298/JSC120901119K; (d) V.R. Narayana, P.K. Zubaidha and R. Varala, Int. J. Org. Chem., 2, 287 (2012); doi:10.4236/ijoc.2012.223039; (e) V.B.C. Figueira, A.G. Esqué, R. Varala, C. González-Bello, S. Prabhakar and A.M. Lobo, Tetrahedron Lett., 51, 2029 (2010); doi:10.1016/j.tetlet.2010.02.048.
  29. S.K. De, J. Mol. Catal. Chem., 225, 169 (2005); doi:10.1016/j.molcata.2004.09.005.
  30. B.C. Ranu, S.S. Dey and A. Hajra, Tetrahedron, 58, 2529 (2002); doi:10.1016/S0040-4020(02)00132-1.
  31. B. Das, R.A. Kumar and P. Thirupathi, Helv. Chim. Acta, 90, 1206 (2007); doi:10.1002/hlca.200790119.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0