One-pot three componenet reaction for the synthesis of 2-alkylthio-3-aroylimidazo[2,1-a]isoquinoline in aqueous media

Heterocycles

Volumn 78, Issue 2, 2009, Pages 415-423

  Kianmehr, Ebrahim ^a   Faramarzi, Reza ^a   Estiri, Hamid ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

Author keywords

Multicomponent Reaction; Phenacyl Bromide; Thiocyanate; Ylide

Indexed keywords

EID: 62649157339     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-11522     Document Type: Article

References (51)

1. Trapani G., Franco M., Ricciardi L., Latrofa A., Genchi G., Sanna E., Tuveri F., Cagetti E., Biggio G., and Liso G. J. Med. Chem. 40 (1997) 3109
2. Gudmundsson K.S., Drach J.C., and Townsend L.B. Tetrahedron Lett. 37 (1996) 6275
3. Gueiffier A., Viols H., Blache Y., Chavignon O., Teulade J.C., Aumelas A., and Chapat J.P. Heterocycles 38 (1994) 551
4. Knölker H.J., Boese R., and Hitzemann R. Chem. Ber 123 (1990) 327
5. Bonnet P.A., Michel A., Laurent F., Sablayrolles C., Rechencq E., Mani J.C., Boucard M., and Chapat J.P. J. Med. Chem. 35 (1992) 3353
6. Yamanaka M., Miyake K., Suda S., Ohhara H., and Ogawa T. Chem. Pharm. Bull. 39 (1991) 1556
7. Starrette Jr. J.E., Montzka T.A., Crosswell A.R., and Cavanagh R.L. J. Med. Chem. 32 (1989) 2204
8. Abignente E., Caprariis P.D., Fattorusso E., and Mayol L. J. Heterocycl. Chem. 26 (1989) 1875
9. Vega J.A., Vaquero J.J., Alvarez-Builla J., Ezquerra J., and Hamdouchi C. Tetrahedron 55 (1999) 2317
10. Dubinsky B., Shriver D.A., Sanfilippo P.J., Press J.B., Tobia A.J., and Rosenthale M.E. Drug Dev. Res. 21 (1990) 277
11. Katsura Y., Nishino S., Inoue Y., Tomoi M., and Takasugi H. Chem. Pharm. Bull. 40 (1992) 371
12. Fisher M.H., and Lusi A. J. Med. Chem. 15 (1972) 982
13. Varma R.S., and Kumar D. Tetrahedron Lett. 40 (1999) 7665
14. Katagiri N., Kato T., and Niwa R. J. Heterocycl. Chem. 21 (1984) 407
15. Kondo T., Kotachi S., Ogino S., and Watanabe Y. Chem. Lett. (1993) 1317
16. Davey D.D. J. Org. Chem. 52 (1987) 1863
17. Galons H., Bergerat I., Farnoux C.C., and Miocque M. Synthesis (1982) 1103
18. Tschitschibabin A.E. Chem. Ber 57 (1924) 2092
19. Kanner C.B., and Pandit U.K. Heterocycles 9 (1978) 757
20. Moutou J.-L., Schmitt M., Collot V., and Bourguignon J.-J. Heterocycles 45 (1997) 897
21. Blackburn C., Guan B., Fleming P., Shiosaki K., and Tsai S. Tetrahedron Lett. 39 (1998) 3635
22. Kroknke F., Kickhofen B., and Thoma C. Chem. Ber 88 (1955) 1117
23. Hand E.S., and Paudler W.W. J. Org. Chem. 43 (1978) 658
24. Tominaga Y., Shiroshita Y., and Hosomi A. Heterocycles 27 (1988) 2251
25. Tominaga Y., and Hosomi A. J. Heterocycl. Chem. 25 (1988) 1449
26. Alcock N.W., Golding B.T., Hall D.R., Horn U., and Watson W.P. J. Chem. Soc., Perkin Trans. 1 (1975) 386
27. Artyomov V.A., Shestopalov A.M., and Litvinov V.P. Synthesis (1996) 927
28. Knölker H.J., and Boese R. J. Chem. Soc., Chem. Commun. (1988) 1151
29. Knölker H.J., and Hitzemann R. Tetrahedron Lett. 35 (1994) 2157
30. Knölker H.J., Boese R., and Hitzemann R. Heterocycles 29 (1989) 1551
31. Potts K.T., and Kanamasa S. J. Org. Chem. 44 (1979) 3803
32. Magatti C.V., and Villani F.J. J. Heterocycl. Chem. 15 (1978) 1021
33. Kröhnke F., and Zecher W. Chem. Ber 95 (1962) 1128
34. Tominaga Y., Motokawa S., Shiroshita Y., and Hosomi A. J. Heterocycl. Chem. 24 (1987) 1365
35. Ito S., Kakehi A., and Miwa T. Heterocycles 32 (1991) 2373
36. Kobayashi Y., Kumadaki I., and Kobayashi E. Heterocycles 15 (1981) 1223
37. Yamanaka H., Egawa H., and Sakamoto T. Chem. Pharm. Bull. 27 (1979) 1004
38. Armstrong R.W., Combs A.P., Tempest P.A., Brown S.D., and Keating T.A. Acc. Chem. Res. 29 (1996) 123
39. Bienaymé H., Hulme C., Oddon G., and Schmitt P. Chem. Eur. J. 6 (2000) 3321
40. Trost B.M. Acc. Chem. Res. 35 (2002) 695
41. Li C.-J., and Chan T.-H. Organic Reactions in Aqueous Media (1997), Wiley, New York
42. Li C.-J. Chem. Rev 93 (1993) 2023
43. Hermann W.A., and Kohlpainter C.W. Angew. Chem., Int. Ed. Engl. 32 (1993) 1524
44. Herrerias C.I., Yao X., Li Z., and Li C.-J. Chem. Rev. 107 (2007) 2546
45. Tomilov Y.V., Platonov D.N., Dorokhov D.V., and Nefedov O.M. Tetrahedron Lett. 48 (2007) 883
46. Vanecko J.A., Wan H., and West F.G. Tetrahedron 62 (2006) 1043
47. Troshin P.A., Peregudova A.S., Peregudova S.M., and Lyubovskaya R.N. Eur. J. Org. Chem. 35 (2007) 5861
48. Li A.-H., Dai L.-X., and Aggarwal V.K. Chem. Rev. 97 (1997) 2341
49. For some physical and chemical properties of water as well as the possible relevance of these properties to aqueous organic chemistry in terms of reactivity, see:
50. In: Li C.-J., and Chan T.-H. (Eds). Comprehensive Organic Reactions in Aqueous Media (2007), Wiley, Noboken, New Jersey
51. Hamdouchi C., de Blas J., del Prado M., Gruber J., Heinz B.A., and Vance L. J. Med. Chem. 42 (1999) 50