Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host

Tetrahedron Letters

Volumn 51, Issue 25, 2010, Pages 3312-3316

  Kanagaraj, Kuppusamy ^a   Pitchumani, Kasi ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Multicomponent reaction; Per 6 ABCD catalysis; Pyranopyrazole; Solvent free conditions

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; KETONE DERIVATIVE; PYRAZOLE DERIVATIVE; SOLVENT;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 77953121188     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.087     Document Type: Article

References (60)

1. Dittmer D.C. Chem. Ind. (1997) 779
2. Tanaka K., and Toda F. Chem. Rev. 100 (2000) 1025
3. Hara K. In: Matsumoto K., and Acheson R.M. (Eds). Organic Synthesis at High Pressures (1991), Wiley, New York 423
4. Ogo Y. Petrotechnology 11 (1988) 307
5. Wang G.-W., Komatsu K., Murata Y., and Shiro M. Nature 387 (1997) 583
6. Varma R.S., Kumar D., and Dahiya R. J. Chem. Res. (S) (1998) 324
7. Nozoe T., Tanimoto K., Takemitsu T., Kitamura T., Harada T., Osawa T., and Takayasu O. Solid State Ionics 141 (2001) 695
8. Lamartine R., and Perrin R. In: Pajonk G.M., Teichner S.J., and Germain J.E. (Eds). Spillover of Adsorbed Species (1983), Elsevier, Amsterdam 251
9. Tsukinoki T., Nagashima S., Mitoma Y., and Tashiro M. Green Chem. 2 (2000) 117
10. Ballini R., Bosica G., Maggi R., Ricciutelli M., Righi P., Sartori G., and Sartorio R. Green Chem. 3 (2001) 178
11. Amantini D., Fringuelli F., Piermatti O., Pizzo F., and Vaccaro L. Green Chem. 3 (2001) 229
12. Ugi I. Pure Appl. Chem. 73 (2001) 187
13. Sheldon R.A. Green Chem. 7 (2005) 267
14. Hailes H.C. Org. Process Res. Dev. 11 (2007) 114
15. El-Tamany E.S., El-Shahed F.A., and Mohamed B.H. J. Serb. Chem. Soc. 64 (1999) 9
16. Ismail Z.H., Aly G.M., El-Degwi M.S., Heiba H.I., and Ghorab M.M. Egypt J. Biot. 13 (2003) 73
17. Zaki M.E.A., Soliman H.A., Hiekal O.A., and Rashad A.E.Z. Naturforsch., C 61 (2006) 1
18. Abdelrazek F.M., Metz P., Metwally N.H., and El-Mahrouky S.F. Arch. Pharm. 339 (2006) 456
19. Abdelrazek F.M., Metz P., Kataeva O., Jaeger A., and El-Mahrouky S.F. Arch. Pharm. 340 (2007) 543
20. Foloppe N., Fisher L.M., Howes R., Potter A., Robertson A.G.S., and Surgenor A.E. Bioorg. Med. Chem. 14 (2006) 4792
21. Kimata A., Nakagawa H., Ohyama R., Fukuuchi T., Ohta S., Suzuki T., and Miyata N. J. Med. Chem. 50 (2007) 5053
22. Junek H., and Aigner H. Chem. Ber. 106 (1973) 914
23. Sosnovskikh V.Y., Barabanov M.A., Usachev B.I., Irgashev R.A., and Moshkin V.S. Russ. Chem. Bull., Int. Ed. 54 (2005) 2846
24. El-Assiery S.A., Sayed G.H., and Fouda A. Acta Pharm. 54 (2004) 143
25. Guard J.A.M., and Steel P.J. ARKIVOC vii (2001) 32
26. Wamhoff H., Kroth E., and Strauch K. Synthesis 11 (1993) 1129
27. Tacconi G., Gatti G., Desimoni G., and Messori V. J. Prakt. Chem. 322 (1980) 831
28. Sharanina L.G., Marshtupa V.P., and Sharanin Y.A. Khim. Geterosikl. Soedin. 10 (1980) 1420
29. Sharanin Y.A., Sharanina L.G., and Puzanova V.V. Zh. Org. Khim. 19 (1983) 2609
30. Rodinovskaya L.A., Gromova A.V., Shestopalov A.M., and Nesterov V.N. Russ. Chem. Bull., Int. Ed. 52 (2003) 2207
31. Otto H.H. Arch. Pharm. 307 (1974) 444
32. Otto H.H., and Schmelz H. Arch. Pharm. 312 (1979) 478
33. Klokol G.V., Krivokolysko S.G., Dyachenko V.D., and Litvinov V.P. Chem. Heterocycl. Compd. 35 (1999) 1183
34. Shestopalov A.M., Emeliyanova Y.M., Shestopalov A.A., Rodinovskaya L.A., Niazimbetova Z.I., and Evans D.H. Tetrahedron 59 (2003) 7491
35. Shestopalov A.M., Emeliyanova Y.M., Shestopalov A.A., Rodinovskaya L.A., Niazimbetova Z.I., and Evans D.H. Org. Lett. 4 (2002) 423
36. Peng Y., Song G., and Dou R. Green Chem. 8 (2006) 573
37. Shi D., Mou J., Zhuang Q., Niu L., Wu N., and Wang X. Synth. Commun. 34 (2004) 4557
38. Jin T.-S., Wang A.-Q., Cheng Z.-L., Zhang J.-S., and Li T.-S. Synth. Commun. 35 (2005) 137
39. Vasuki G., and Kumaravel K. Tetrahedron Lett. 49 (2008) 5636
40. Lehmann F., Holm M., and Laufer S. J. Comb. Chem. 10 (2008) 364
41. Zhou J.-F., Tu S.-J., Zhu H.-Q., and Zhi S.-J. Synth. Commun. 32 (2002) 3363
42. Shaker R.M., Mahmoud A.F., and Abdel-Latif F.F. J. Chin. Chem. Soc. 52 (2005) 563
43. Guo S.-B., Wang S.-X., and Li J.-T. Synth. Commun. 37 (2007) 2111
44. Ren Z., Cao W., Tong W., and Jin Z. Synth. Commun. 35 (2005) 2509
45. Nagarajan A.S., and Reddy B.S.R. Synlett (2009) 2002
46. Takahashi K. Chem. Rev. 98 (1998) 2013
47. Sakuraba H., and Maekawa H. J. Inclusion Phenom. Macrocycl. Chem. 54 (2006) 41
48. Bhosale S.V., and Bhosale S.V. Mini-Rev. Org. Chem. 4 (2007) 231
49. Wenz G. Angew. Chem., Int. Ed. Engl. 33 (1994) 803
50. In: Dodziuk H. (Ed). Cyclodextrin and their Complexes (2006), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
51. McCracken P.G., Ferguson C.G., Vizitiu D., Walkinshaw C.S., Wang Y., and Thatcher G.R.J. J. Chem. Soc., Perkin Trans. 2 (1999) 911
52. Kitae T., Nakayama T., and Kano K. J. Chem. Soc., Perkin Trans. 2 (1998) 207
53. Riela S., D'Anna F., Meo L.P., Gruttadauria M., Giacalone R., and Noto R. Tetrahedron 62 (2006) 4323
54. Brown S.E., Coates J.H., Duckworth P.A., Lincoln S.F., Easton C.J., and May B.L. J. Chem. Soc., Faraday Trans. 89 (1993) 1035
55. Suresh P., and Pitchumani K. J. Org. Chem. 73 (2008) 9121
56. Suresh P., and Pitchumani K. Tetrahedron: Asymmetry 19 (2008) 2037
57. 13C-NMR and mass spectral techniques (see Supplementary data).
58. Ashton P.R., Koniger R., and Stoddart J.F. J. Org. Chem. 61 (1996) 903
59. Petter R.C., Salek J.S., Sikorski C.T., Kumaravel G., and Lin F.-T. J. Am. Chem. Soc. 112 (1990) 3860
60. Tang W., and Ng S.-C. Nat. Protocols 3 (2008) 691