Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides

Tetrahedron Letters

Volumn 55, Issue 33, 2014, Pages 4657-4660

  Yaragorla, Srinivasarao ^a   Singh, Garima ^a   Lal Saini, Pyare ^a   Reddy, M Kesava ^a  

^a CENTRAL UNIVERSITY OF RAJASTHAN   (India)

Author keywords

Atom economy; Ca(II) catalysis; Green synthesis; Microwave irradiation; Ritter reaction

Indexed keywords

ALKENE DERIVATIVE; AMIDE; CALCIUM ION; NITRILE; SULFURIC ACID;

ARTICLE; CATALYST; FRIEDEL CRAFTS REACTION; HIGH TEMPERATURE; MICROWAVE IRRADIATION; NUCLEOPHILICITY; PROTON TRANSPORT; REACTION TIME; SYNTHESIS;

EID: 84908137711     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.06.068     Document Type: Article

References (57)

1. C.E. Mabermann J.I. Kroschwitz, Encyclopedia of Chemical Technology 1 1991 Wiley New York 251 266
2. D. Lipp J.I. Kroschitz, Encyclopedia of Chemical Technology 1 1991 Wiley New York 266 287
3. R. Opsahl J.I. Kroschwitz, Encyclopedia of Chemical Technology Vol. 2 1991 Wiley New York 346 356
4. J.M. Humphrey, and A.R. Chamberlin Chem. Rev. 97 1997 2243
5. J.W. Bode Curr. Opin. Drug Discov. Dev. 9 2006 765
6. T. Cupido, J. Tulla-Puche, J. Spengler, and F. Albericio Curr. Opin. Drug Discov. Dev. 10 2007 768
7. Greenberg, A.; Breneman, C. M.; Liebman, J. F. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science, Wiley - Intersciences: New York, 2000, pp. 33-45. (ISBN: 978-0-471-42025-5).
8. A. Khalafi-Nezhad, A. Parhami, M.N.S. Rad, and A. Zarea Tetrahedron Lett. 46 2005 6879
9. S.-Y. Han, and Y.-A. Kim Tetrahedron 60 2004 2447
10. C.A.G.N. Montalbetti, and V. Falque Tetrahedron 61 2005 10827
11. E. Valeur, and M. Bradley Chem. Soc. Rev. 38 2009 606
12. M. Hosseini-Sarvari, and H. Sharghi J. Chem. Res. 2006 205
13. J.A. Sanguigni, and R. Levine J. Med. Chem. 7 1964 573
14. J. Joubert, S. vanDyk, I.R. Greenand, and S.F. Malan Bioorg. Med. Chem. 19 2011 3935 3944
15. E.I. Bagrii Adamantany: Poluchenie, Svoistva, Primenenie, (Adamantans: Production, Properties, Application) 1989 Nauka Moscow 264
16. G.S. Singh Tetrahedron 59 2003 7631
17. R. Breslow, R. Fairweather, and J. Keana J. Am. Chem. Soc. 89 1967 2135
18. G. Villain, A. Gaset, and P. Kalck J. Mol. Catal. 12 1981 103
19. S.-I. Murahashi, S. Sasao, E. Saito, and T. Naota J. Org. Chem. 57 1992 2521
20. J.H. Kim, J. Britten, and J. Chin J. Am. Chem. Soc. 115 1993 3618
21. Y. Tamaru, Y. Yamada, and Z. Yoshida Synthesis 1983 474
22. T. Naota, and S.-I. Murahashi Synlett 1991 693
23. J.J. Ritter, and P.P. Minieri J. Am. Chem. Soc. 70 1948 4045
24. F.R. Densonand, and J.J. Ritter J. Am. Chem. Soc. 71 1949 4128
25. L.I. Krimen, and D.J. Cota Org. React. 17 1969 213
26. M.Y. Lebedev, and M.B. Erman Tetrahedron Lett. 43 2002 1397
27. V. JustriboÍ, and M.I. Colombo Tetrahedron Lett. 44 2003 8023
28. E. Callens, A.J. Burtonb, and A.G.M. Barretta Tetrahedron Lett. 47 2006 8699
29. F. Tamaddon, M. Khoobi, and E. Keshavarz Tetrahedron Lett. 48 2007 3643
30. T. Okuhara, and X. Chen Microporous Mesoporous Mater. 48 2001 293 and reference cited therein
31. A.G. Martinez, R.M. Alvarez, E.T. Vilar, A.G. Fraile, M. Hanack, and L.R. Subramanian Tetrahedron Lett. 30 1989 581
32. H. Firouzabadi, A.R. Sardarian, and H. Badparva Synth. Commun. 27 1973 2403
33. R. Sanz, A. Martinez, V. Guilarte, J.M. Alvarez-Gutierrezand, and F. Rodriguez Eur. J. Org. Chem. 2007 4642
34. L. Ma'mani, A. Heydari, and M. Sheykhan Appl. Catal., A 384 2010 122
35. M. Mukhopadhyay, M.M. Reddy, G.G. Maikap, and J. Iqbal J. Org. Chem. 60 1995 2670
36. G.A. Olah, T. Yamato, P.S. Iyer, N.J. Trivedi, B.P. Singh, and G.K. Surya Prakash Mater. Chem. Phys. 17 1987 21
37. T. Yamato, J.Y. Hu, and N. Shinoda J. Chem. Res. 11 2007 641
38. V. Polshettiwar, and R.S. Varma Tetrahedron Lett. 49 2008 2661
39. R.K. Rapolu, B. Nabamukul, S.R. Bommineni, R. Potham, N. Mulakayala, and S. Oruganti RSC Adv. 3 2013 5332
40. G.D.A. John, A.C. Jeremy, L. Christian, J.O. Danica, W.R. Kyle, and M. Donna Synth. Commun. 43 2013 3224 3232
41. B.V.S. Reddy, N.S. Reddy, C. Madanand, and J.S. Yadav Tetrahedron Lett. 51 2010 4827
42. R.G. Kalkhambkar, S.N. Waters, and K.K. Laali Tetrahedron Lett. 52 2011 867
43. G.A. Olah, B.G.B. Guptaand, and S.C. Narang Synthesis 1979 274
44. T. Luigino, P. Emanuela, S. Valentina, and T. Piera Tetrahedron: Asymmetry 20 2009 368 374
45. L.U. Nordstrom, H. Vogt, and R. Madsen J. Am. Chem. Soc. 130 2008 17672 17673
46. K. Niknam, M.A. Zolfigol, and T. Sadabadi J. Iran. Chem. Soc. 4 2007 199 204
47. J.-M. Begouin, and M. Niggemann Chem. Eur. J. 19 2013 8030 8041
48. N.V. Forkel, D.A. Henderson, and M.J. Fuchter Green Chem. 14 2012 2129
49. M. Niggemann, and M.J. Meel Angew. Chem., Int. Ed. 49 2010 3684 3687
50. A.K. Diba, J.-M. Begouin, and M. Niggemann Tetrahedron Lett. 53 2012 6629 6632
51. S. Yaragorla, and G.S. Kumar Indian J. Chem., Sect. B 2014 (3/4OC1661)
52. S. Yaragorla, A. Sudhakar, and N. Kiranmai Indian J. Chem., Sect. B 2014 (3/4OC1688)
53. P. Theerthagiri, A. Lalithaand, and P.N. Arunachalam Tetrahedron Lett. 51 2010 2813
54. A. Bruno, G. Amandine, R. Sébastien, and C. Janine Tetrahedron Lett. 50 2009 3470 3473
55. W. Song, L. Ma, and L. Hu Synth. Commun. 41 2011 3186 3196
56. T. Niwa, H. Yorimitsu, and K. Oshima Org. Lett. 10 2008 4689 4691
57. Margherita Barbero Eur. J. Org. Chem. 3 2009 430 436