An efficient, catalyst- and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding

Tetrahedron

Volumn 64, Issue 3, 2008, Pages 536-542

  Kumar, Satish ^a   Sharma, Poonam ^a   Kapoor, Kamal K ^a   Hundal, Maninder Singh ^b  

^a UNIVERSITY OF JAMMU   (India)

^b GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Catalyst free; Grinding; Hantzsch condensation; One pot synthesis; Polyhydroquinolines; Solvent free

Indexed keywords

QUINOLINE DERIVATIVE; SOLVENT;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; GRINDING; PRIORITY JOURNAL; PURIFICATION; REACTION ANALYSIS; REACTION TIME; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 36549074210     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.11.008     Document Type: Article

References (50)

1. Bossert F., Meyer H., and Wehinger E. Angew. Chem., Int. Ed. Engl. 20 (1981) 762-769
2. Nakayama H., and Kasoaka Y. Heterocycles 42 (1996) 901-909
3. Godfraid T., Miller R., and Wibo M. Pharmocol. Rev. 38 (1986) 321-327
4. Sausins A., and Duburs G. Heterocycles 27 (1988) 279-289
5. Mager P.P., Coburn R.A., Solo A.J., Triggle D.J., and Rothe H. Drug Des. Discov. 8 (1992) 273-289
6. Mannhold R., Jablonka B., Voigt W., Schonafinger K., and Schraven K. Eur. J. Med. Chem. 27 (1992) 229-235
7. Klusa V. Drugs Future 20 (1995) 135-138
8. Bretzel R.G., Bollen C.C., Maester E., and Federlin K.F. Am. J. Kidney Dis. 21 (1993) 54-63
9. Bretzel R.G., Bollen C.C., Maester E., and Federlin K.F. Drugs Future 17 (1992) 465-468
10. Boer R., and Gekeler V. Drugs Future 20 (1995) 499-509
11. Chen Y.L., Fang K.-C., Sheu J.-Y., Hsu S.-L., and Tzeng C.-C. J. Med. Chem. 44 (2001) 2374-2377
12. Roma G., Braccio M.D., Grossi G., and Chia M. Eur. J. Med. Chem. 35 (2000) 1021-1035
13. Maguire M.P., Sheets K.R., McVety K., Spada A.P., and Zilberstein A. J. Med. Chem. 37 (1994) 2129-2137
14. Sainani J.B., Shah A.C., and Arya V.P. Indian J. Chem., Sect. B 33 (1994) 526-531
15. Ahluwalia V.K., Goyal B., and Das U. J. Chem. Res., Synop. (1997) 266
16. Margarita S., Estael O., Yamila V., Beatriz P., Lourdes M., Nazario M., Margarita Q., Carlos S., Jose L.S., Hector N., Norbert B., and Oswald M.P. Tetrahedron 55 (1999) 875-884
17. Ahluwalia V.K., Goyal B., and Das U. J. Chem. Res., Miniprint 7 (1997) 1701-1715
18. Ahluwalia V.K., and Goyal B. Indian J. Chem., Sect. B 35 (1996) 1021-1025
19. Margarita S., Yamila V., Estael M., Nazario M., Roberto M., Margaria Q., Carlos S., Jose S., Hector L.N., Norbert B., Oswald M., and Camiel D. J. Heterocycl. Chem. 37 (2000) 735
20. Ohberg L., and Westman J. Synlett (2001) 1296
21. Agarwal A., and Chauhan P.M.S. Tetrahedron Lett. 46 (2005) 1345-1348
22. Tu S., Zhang J., Zhu X., Zhang Y., Wang Q., Xu J., Jiang B., Jia R., Zhang J., and Shi F. J. Heterocycl. Chem. 43 (2006) 985-989
23. Ji S.-J., Jiang Z.-Q., Lu J., and Loh T.-P. Synlett (2004) 831-835
24. Sridhar R., and Perumal P.T. Tetrahedron 61 (2005) 2465-2470
25. Sabitha G., Reddy G.S.K.K., Reddy C.S., and Yadav J.S. Tetrahedron Lett. 44 (2003) 4129-4131
26. Wang L.-M., Sheng J., Zhang L., Han J.-W., Fan Z., Tian H., and Qian C.-T. Tetrahedron 61 (2005) 1539-1543
27. Ko S., Sastry M.N.V., Lin C., and Yao C.-F. Tetrahedron Lett. 46 (2005) 5771-5774
28. Ko S., and Yao C.-F. Tetrahedron 62 (2006) 7293-7299
29. Legeay J.C., Goujon J.Y., Eynde J.J.V., Toufet L., and Bazureau J.P. J. Comb. Chem. 8 (2006) 829-833
30. Dondoni A., Massi A., Minghini E., and Bertolasi V. Tetrahedron 60 (2004) 2311-2326
31. Kumar A., and Maurya R.A. Tetrahedron 63 (2007) 1946-1952
32. Rothenberg G., Downie A.P., Raston C.L., and Scott J.L. J. Am. Chem. Soc. 123 (2002) 8701-8708
33. Toda F., Takumi H., and Yamaguchi H. Chem. Express 4 (1989) 507-510
34. Tanaka K., Kishigami S., and Toda F. J. Org. Chem. 56 (1991) 4333-4334
35. Toda F., Tanaka K., and Hamai K. J. Chem. Soc., Perkin Trans. 1 (1990) 3207-3209
36. Toda F., Suzuki T., and Higa S. J. Chem. Soc., Perkin Trans. 1 (1998) 3521-3522
37. Ren Z.-J., Cao W.-G., and Tong W.-Q. Synth. Commun. 32 (2002) 3475-3479
38. Toda F., Kiyoshige K., and Yagi M. Angew. Chem., Int. Ed. Engl. 101 (1989) 329-330
39. Ren Z.-J., Cao W.-G., Ding W.-Y., and Shi W. Synth. Commun. 34 (2004) 4395-4400
40. Ren Z., Cao W., Tong W., and Jin Z. Synth. Commun. 35 (2005) 2509-2513
41. Schmeyers T., Toda F., Boy J., and Kaupp G. J. Chem. Soc., Perkin Trans. 2 (1998) 989-993
42. Clarke P.A., Santos S., and Martin W.H.C. Green Chem. (2007) 438-440
43. Kumar A., Kumar S., and Kapoor K.K. Aust. J. Chem. 60 (2007) 621-623
44. Mahajan D., Ganai B.A., Sharma R.L., and Kapoor K.K. Tetrahedron Lett. 47 (2006) 7919-7921
45. Ganai B.A., Kumar S., Andotra C.S., and Kapoor K.K. Synth. Commun. 36 (2006) 803-807
46. Kapoor K.K., Ganai B.A., Kumar S., and Andotra C.S. Synth. Commun. 36 (2006) 2727-2735
47. XSCANS, X-ray Single Crystal System, Version 2.1 (1994), Siemens Analytical X-ray Instruments, Madison, WI
48. Sheldrick G.M. SHELXTL-PC, Release 5.03 (1995), Siemens Analytical X-ray Instruments, Madison, WI
49. Farrugia, L. J. WINGX (version 1.70.01), An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single-Crystal X-ray Diffraction Data. University of Glasgow: Glasgow, 2005;
50. Nardelli M. Comput. Chem. (1983) 95