Nanocrystalline copper(II) oxide catalyzed aza-Michael reaction and insertion of α-diazo compounds into N-H bonds of amines

Tetrahedron Letters

Volumn 50, Issue 31, 2009, Pages 4467-4469

  Kantam, M Lakshmi ^a   Laha, Soumi ^a   Yadav, Jagjit ^a   Jha, Shailendra ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

, Unsaturated compounds; Aza Michael addition; Diazoacetate; Heterogeneous catalyst; Insertion; Nanocrystalline copper(II) oxide

Indexed keywords

ALIPHATIC AMINE; CUPRIC OXIDE; DIAZOACETIC ACID ETHYL ESTER; GLYCINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; MICHAEL ADDITION;

EID: 66949146543     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.059     Document Type: Article

References (56)

1. Bartoli G., Cimarelli C., Marcantoni E., Palmieri G., and Petrini M. J. Org. Chem. 59 (1994) 5328
2. Wang Y.F., Izawa T., Kobayashi S., and Ohno M. J. Am. Chem. Soc. 104 (1982) 6465
3. Wabnitz T.C., and Spencer J.B. Chem. Eur. J. 10 (2004) 484
4. Liu M., and Sibi M.P. Tetrahetron 58 (2002) 7991
5. Hayashi Y., Rode J.J., and Corey E.J. J. Am. Chem. Soc. 118 (1996) 5502
6. Eliel E.L., and He X. J. Org. Chem. 55 (1990) 2114
7. Srivastava N., and Banik B.K. J. Org. Chem. 68 (2003) 2109
8. Vala R., Alam M.M., and Adapa S.R. Synlet (2003) 720
9. Jenner G. Tetrahedron Lett. 36 (1995) 233
10. Matsubara M., Yoshioka M., and Utimoto K. Chem. Lett. (1994) 827
11. Loh T.P., and Wei L.L. Synlett (1998) 975
12. Xu L.W., Li L., and Xia C.G. Helve. Chim. Acta 87 (2004) 1522
13. Fadini L., and Tongi A. Chem Commun. (2003) 30
14. Azizi N., and Saidi M.R. Tetrahedron 60 (2004) 383
15. Xu L.W., Li J.W., Xia C.G., Zhou S.L., and Hu X.X. Synlett (2003) 2425
16. Cabral J., Laszlo P., Mahe L., Montaufier M.T., and Randriamahefa S.L. Tetrahedron Lett. 30 (1989) 3969
17. Shaikh N.S., Despande V.H., and Bedekar A.V. Tetrahedron 57 (2001) 9045
18. Basu B., Das P., and Hossain I. Synlett (2004) 2630
19. Bartoli G., Bartolacci M., Giuliani A., Marcantoni E., Massaccesi M., and Torregiani E. J. Org. Chem. 70 (2005) 169
20. Yadav J.S., Reddy B.V.S., Basak A.K., and Narsaiah A.V. Chem. Lett. (2003) 988
21. Xu L.-W., Li J.-W., Zhou S.-L., and Xia C.-G. New J. Chem. 28 (2004) 183
22. Ye T., and McKarvey M.A. Chem. Rev. 94 (1994) 1091
23. Doyle M.P. Chem. Rev. 86 (1986) 919
24. For pharmaceutical application of carbenoid chemistry, see:. Andreoli P., Cainelli G., Panunzio M., Bandini E., Martelli G., and Spunta G. J. Org. Chem. 56 (1991) 5984
25. Reider P.J., and Grabowski E.J.J. Tetrahedron Lett. 23 (1982) 2293
26. Ratcliffe R.W., Salzmann T.N., and Christensen B.G. Tetrahedron 21 (1980) 31
27. Karady S., Amato J.S., Reamer R.A., and Weinstock L.M. J. Am. Chem. Soc. 103 (1981) 6765
28. Wentrup C., and Winter H.-W. J. Am. Chem. Soc. 102 (1980) 6161
29. Yates P. J. Am. Chem. Soc. 74 (1952) 5376
30. Saegusa T., Ito Y., Kobayashi S., Hirota K., and Shimizu T. Tetrahedron Lett. 7 (1966) 6131
31. Nicoud J.-F., and Kagan H.B. Tetrahedron Lett. 12 (1971) 2065
32. Paulissen R., Hayez E., Hubert A.J., and Teyssie P. Tetrahedron Lett. 15 (1974) 607
33. Osipov S.N., Sewald N., Kolomiets A.F., Fokin A.V., and Berger K. Tetrahedron Lett. 37 (1996) 615
34. Aller E., Buck R.T., Drysdale M.J., Ferris L., Haigh D., Moody C.J., Pearson N.D., and Sanghera J.B. J. Chem. Soc., Perkin Trans. 1 (1996) 2879
35. Ferris L., Haigh D., and Moody C.J. J. Chem. Soc., Perkin Trans. 1 (1996) 2885
36. Bashford K.E., Cooper A.L., Kane P.D., and Moody C. J. Chem. Soc., Perkin Trans. 1 (2002) 1672
37. Galardon E., Maux P.l., and Simonneaux G. J. Chem. Soc., Perkin Trans. 1 (1997) 2455
38. Morilla M.E., Diaz-Requejo M.M., Belderrain T.R., Nicasio M.C., Trofimenko S., and Perez P.J. Chem. Commun. (2002) 2998
39. Bachmann S., Fielenbach D., and Jorgensen K.A. Org. Biomol. Chem. 2 (2004) 3044
40. Itoh H., Utamapanya S., Stark J.V., Klabunde K.J., and Schlup J.R. Chem. Mater. 5 (1993) 71
41. Jiang Y., Decker C., Mohs C., and Klabunde K.J. J. Catal. 180 (1998) 24
42. Guzman J., and Gates B.C. Nano Lett. 1 (2001) 689
43. Choudary B.M., Mulukutla R.S., and Klabunde K.J. J. Am. Chem. Soc. 125 (2003) 2020
44. Shi F., Tse M.K., Pohl M.-M., Brückner A., Zhang S., and Beller M. Angew. Chem., Int. Ed. 46 (2007) 8866
45. Polshettiwar V., and Varma R.S. Chem. Eur. J. 15 (2009) 1582
46. Polshettiwar V., and Varma R.S. Org. Biomol. Chem. 7 (2009) 37
47. Polshettiwar V., Baruwati B., and Varma R.S. Green Chem. 11 (2009) 127
48. Polshettiwar V., Baruwati B., and Varma R.S. Chem. Commun. (2009) 1837
49. Larsson P., and Andersson A. J. Catal. 179 (1998) 72
50. Chikán V., Molnár A., and Balázsik K. J. Catal. 184 (1999) 134
51. c Superconducting Copper Oxides (1991), Springer, Berlin
52. Poole C.P., Datta T., Farach H.A., Rigney M.M., and Sanders C.R. Copper Oxide Superconductors (1988), John Wiley & Sons, NewYork
53. Choudary B.M., Ranganath K.V.S., Yadav J., and Kantam M.L. Tetrahedron Lett. 46 (2005) 1369
54. Kantam M.L., Laha S., Yadav J., Choudary B.M., and Sreedhar B. Adv. Synth. Catal. 348 (2006) 867
55. Kantam M.L., Shiva Kumar K.B., and Sridhar Ch. Adv. Synth. Catal. 347 (2005) 1212
56. Choudary B.M., Ranganath K.V.S., Pal U., Kantam M.L., and Sreedhar B. J. Am. Chem. Soc. 127 (2005) 13167