One-pot three-component Mannich-type reactions using Sulfamic acid catalyst under ultrasound irradiation

Ultrasonics Sonochemistry

Volumn 16, Issue 6, 2009, Pages 758-762

  Zeng, Hongyao ^a,b   Li, Hua ^a,b   Shao, Huawu ^a,b  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Mannich reaction; One pot reaction; Sulfamic acid; Ultrasound; Aminocarbonyl compound

Indexed keywords

AMINES; CATALYSTS; CHEMICAL REACTIONS; KETONES; ULTRASONICS;

AMINOCARBONYL COMPOUND; ENVIRONMENTAL POLLUTIONS; GREEN CATALYSTS; MANNICH REACTIONS; MANNICH-TYPE REACTIONS; ONE-POT REACTION; SUBSTITUTED AROMATIC; ULTRASOUND IRRADIATION;

SULFAMIC ACID;

ACID; ALDEHYDE; AMINE; AROMATIC AMINE; CARBONYL DERIVATIVE; KETONE; SULFAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; MANNICH REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION OPTIMIZATION; ULTRASOUND;

EID: 67349278502     PISSN: 13504177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2009.03.008     Document Type: Article

References (47)

1. Cordova A. Acc. Chem. Res. 37 (2004) 102
2. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069
3. Arend M., Westermann B., and Risch N. Angew. Chem. Int. Ed. 37 (1998) 1044
4. Mannich C., and Krosche W. Arch. Pharm. 250 (1912) 674
5. Müller R., Goesmann H., and Waldmann H. Angew. Chem. Int. Ed. 38 (1999) 184
6. Bohme H., and Haake M. In: Taylor E.C. (Ed). Advances in Organic Chemistry (1976), John Wiley and Sons, New York 107
7. For comprehensive reviews:. Arend M., Westermann B., and Risch N. Angew. Chem. Int. Ed. Engl. 37 (1998) 1044 (and references cited therein)
8. Tramontini M., and Angiolini L. Mannich-Bases. Chemistry and Uses (1994), CRC, Boca Raton, FL (and reference cited therein)
9. Volkmann R.A. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 1 (1991), Pergamon, Oxford 355 (and references cited therein)
10. Kobayashi S., Hamada T., and Manabe K. J. Am. Chem. Soc. 124 (2002) 5640
11. Kobayashi S., Matsubara R., and Kitagawa H. Org. Lett. 4 (2002) 143
12. Periasamy M., Suresh S., and Ganesan S.S. Tetrahedron Lett. 46 (2005) 5521
13. Jacobsen M.F., Ionita L., and Skrydstrup T. J. Org. Chem. 69 (2004) 4792
14. Komoto I., and Kobayashi S. J. Org. Chem. 69 (2004) 680
15. Chung W.J., Omote M., and Welch J.T. J. Org. Chem. 70 (2005) 7784
16. Ollevier T., and Nadeau E. J. Org. Chem. 69 (2004) 9292
17. List B., Pojarliev P., Biller W.T., and Martin H.J. J. Am. Chem. Soc. 124 (2002) 827
18. List B. J. Am. Chem. Soc. 122 (2000) 9336
19. Duthaler R.O. Angew. Chem. Int. Ed. 42 (2003) 975
20. Hayashi Y., Tsuboi W., Ashimine I., Urushima T., Shoji M., and Sakai K. Angew. Chem. Int. Ed. 42 (2003) 3677
21. Kantam M.L., Rajasekhar Ch.V., Gopikrishna G., Reddy K.R., and Choudary B.M. Tetrahedron Lett. 47 (2006) 5965
22. Manabe K., Mori Y., and Kobayashi S. Tetrahedron 57 (2001) 2537
23. Manabe K., and Kobayashi S. Org. Lett. 1 (1999) 1965
24. Wang R., Li B.G., Huang T.K., Shi L., and Lu X.X. Tetrahedron Lett. 48 (2007) 2071
25. Yi W.B., and Cai C. J. Fluorine Chem. 127 (2006) 1515
26. Wang L.M., Han J.W., Sheng J., Tian H., and Fan Z.Y. Catal. Commun. 6 (2005) 201
27. Wang L.M., Han J.W., Sheng J., Fan Z.Y., and Tian H. Chin. J. Org. Chem. 25 (2005) 591
28. Sahoo S., Joseph T., and Halligudi S.B. J. Mol. Catal. A: Chem. 244 (2006) 179
29. Li Z., Ma X.L., Liu J., Feng X., Tian G.Q., and Zhu A.G. J. Mol. Catal. A: Chem. 272 (2007) 132
30. Jin T.S., Sun G., Li Y.W., and Li T.S. Green Chem. 4 (2002) 255
31. Li J.T., Han J.F., Yang J.H., and Li T.S. Ultrason. Sonochem. 10 (2003) 119
32. Patil S.B., Singh P.R., Surpur M.P., and Samant S.D. Ultrason. Sonochem. 14 (2007) 515
33. Li J.T., Dai H.G., Xu W.Z., and Li T.S. Ultrason. Sonochem. 13 (2006) 24
34. Wang B., Yang L.M., and Suo J.S. Tetrahedron Lett. 44 (2003) 5037
35. Wang B., Gu Y.L., Luo C., Yang T., Yang L.M., and Suo J.S. Tetrahedron Lett. 45 (2004) 369
36. Yadav J.S., Rao P.P., Sreenu D., Rao R.S., Kumar V.N., Nagaiah K., and Prasad A.R. Tetrahedron Lett. 46 (2005) 7249
37. Heydari A., Khaksar S., Pourayoubi M., and Mahjoub A.R. Tetrahedron Lett. 48 (2007) 4059
38. An L.T., Zou J.P., Zhang L.L., and Zhang Y. Tetrahedron Lett. 48 (2007) 4297
39. Upadhyaya D.J., Barge A., Stefania R., and Cravotto G. Tetrahedron Lett. 48 (2007) 8318
40. Nagarajan R., Magesh C.J., and Perumal P.T. Synthesis (2004) 69
41. Sing P.R., Singh D.U., and Samant S.D. Synlett (2004) 1909
42. Xia M., and Liu Y.D. J. Fluorine Chem. 127 (2006) 1119
43. Doble M., and Kumar A. Green Chemistry and Engineering (2007), Elsevier
44. Luche J.L. Synthetic Organic Sonochemistry (1998), Plenum Press, New York
45. Mason T.J., and Peters D. Practical Sonochemistry. second ed. (2002), EllisHorwood, London
46. Cravotto G., and Cintas P. Chem. Soc. Rev. 35 (2006) 180
47. Zeng H.Y., Yin S.F., and Li Y. Chin. J. Org. Chem. 27 (2007) 528