Ultrasound Assisted Copper (I) Catalyzed Conjugate Addition of Heterocyclic bromides to 1, 1-Diacetate

Authors

  • Ashok S. Pise  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Arvind S. Burungale  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Ramesh B. Gawade  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Santosh S. Devkate  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Sunil D. Jadhav  Department of Chemistry, Mahatma Phule Mahavidyalaya, Panvel, Raigad, Maharashtra, India
  • Mohan B. Kale  Department of Chemistry, Mahatma Phule Mahavidyalaya, Panvel, Raigad, Maharashtra, India

Keywords:

Conjugate addition, Diacetate, Cu (I) catalyst, Heterocyclic bromides, Ultrasound irradiation.

Abstract

1,1-Diacetate was prepared from cinnamaldehyde and acetic anhydride by reported method. The conjugated addition products were synthesized from heterocyclic bromides and 1,1-diacetate in the presence of 10 mol % Cu (I) catalyst in high yields within 15-25 min. under ultrasound irradiation.

References

  1. C. Narayana, S. Padmanabhan and G. W. Kabalka, Tetrahedron Lett, (1990),31, 6977.
  2. R. S. Varma, A.K. Chatterjee and M. Varma Tetrahedron Lett, (1993), 34, 3207.
  3. R. G. Sudhakar, R. Radhika, N. Parvathi & D. S. Iyengar, Indian J. Chem. (2002), 41B. 863.
  4. K. S. Kochhar, B. S. Bal, R. P. Deshpande, S. N. Rajadhyaksha & H. W. Pinnick, J. Org. Chem,(1983), 48, 1765.
  5. F. Freeman & E. M. Karchefski, J. Chem. Eng. Data, (1997), 22, 355. 
  6. G. A. Olah, & A. K. Karcherski, Synthesis, (1982), 962. 
  7. I. Scriabine, Bull Chim Soc Fr. (1961), 1194.
  8. J. K. Michie & J. A. Miller, Synthesis, (1981), 824.
  9. C. Dupuy, C. Petrier, L. A. Sarandeses & J. L. Luche, Synth. Commun. (1991), 21, 643. 
  10. P.Knochel Handbook of Functionalized organometallics Wiley-VCH ISBH 3-527-31131-9 Vol. 1 Chapter 7, (2005). 
  11. Paul Knochel, Juan J., Almena Perea and Philip Jones Tetrahedron, (1998), 54, 8275-8319.
  12. E. Negishi Organometallics in Organic Synthesis, Vol. 1 Wiley New York, (1980).
  13. I. Antes, G. Frenking, Organometallics, (1995), 14, 4263.
  14. United States Patent US005756653A Patent number 5756653 26 May (1998).
  15. B. H. Lipshutz, S. Seugepta Org. React. (1992), 41, 135.
  16. B. H. Lipshutz, P.A. Blomgren, S. K. Kim Tetrahedron Lett. (1999), 40, 197.
  17. C. Dai, G. C. Fu, J. Am. Chem. Soc. (2001), 123, 2719.
  18. J. Z. Deng, D. V. Pone, A. T. Ginnetti, Kurihara H. S. D Dreher Org. Lett.(2009), 11, 345-347.
  19. Voisin-Chiret, A. S. Bouillon, A. Burzicki, G. Celant, M. Tetrahedron, (2009), 65, 607-612.
  20. Schwab P. F. H. Fleischer F. Michl J. J. Org. Chem. (2002), 67, 443-449.
  21. J. J. Song, N. K. Yee, Z. Tan, J. Xu, S. R. Kapadia, C. H. Senanayake Org. Lett. (2004), 6, 4905-4907.
  22. X. F. Duan, Z. Q. Ma, F. Zhang Z. B. J. Zhang Org. Chem. (2009), 74, 939-942.
  23. Y. Q. Fang, G. S. Hanan Syn. Lett. (2003), 852-854.
  24. Y. A. Getmanenko, R. J. J. Twieg Org. Chem. (2008),73, 830-839.
  25. A. S. Burungale, R. B. Gawade, A. S. Pise, S. S. Devkate and S. D. Jadhav IJSRST(2017), 3, 9, 90-94. 
  26. S. S. Devkate, A. S. Burungale, S.D Jadhav, A. S. Pise, R. B. Gawade and M. B. Kale, IJSRST(2017), 3, 8, 998-1001.

International Journal of Scientific Research in Science and Technology

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Published

2018-02-28

Issue

Volume 4, Issue 2, January-February-2018

Section

Research Articles

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How to Cite

[1]
Ashok S. Pise, Arvind S. Burungale, Ramesh B. Gawade, Santosh S. Devkate, Sunil D. Jadhav, Mohan B. Kale, " Ultrasound Assisted Copper (I) Catalyzed Conjugate Addition of Heterocyclic bromides to 1, 1-Diacetate, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 4, Issue 2, pp.446-449, January-February-2018.