A novel, fast and efficient one-pot four-component procedure for preparation of some alkyl spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylates

Journal of the Iranian Chemical Society

Volumn 7, Issue 1, 2010, Pages 45-50

  Alizadeh Karsalary, A ^a   Mohammadizadeh, M R ^b   Hasaninejad, A R ^b   Mohammadi, A A ^c   Karimi, A R ^d  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b PERSIAN GULF UNIVERSITY   (Iran)

^c SHAHID BEHESHTI UNIVERSITY   (Iran)

^d ARAK UNIVERSITY   (Iran)

Author keywords

Alkyl acrylates; Alkyl spiro indeno 1,2 b quinoxaline 11,3' pyrrolizine 2' carboxylates; Ninhydrin; Phenylenediamines; Proline

Indexed keywords

EID: 77749316231     PISSN: 1735207X     EISSN: 17352428     Source Type: Journal    
DOI: 10.1007/bf03245858     Document Type: Article

References (53)

1. For a monograph, see: J. Zhu, H. Bienayme, Multi-component reactions, VCH, Weinhein, Germany, 2005.
2. For reviews, see: A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39 (2000) 3169;
3. I. Ugi, S. Heck, Comb. Chem. High Throughput Screen 4 (2001) 1.
4. L. Weber, Drug Discovery Today 7 (2002) 143.
5. C. Hulme, V. Gore, Curr. Med. Chem. 10 (2003) 51.
6. R.V.A Orru, M. de Greef, Synthesis (2003) 1471.
7. D.J. Ramon, M. Yus, Angew. Chem. Int. Ed. 44 (2005) 1602.
8. M. Syamala, Org. Prep. Proced. Int. 37 (2005) 103.
9. A. Domling, Chem. Rev. 106 (2006) 17.
10. For selected recent examples, see: C. Montagne, J.J. Shiers, M. Shipman, Tetrahedron Lett. 47 (2006) 9207.
11. M.S.A. Dondoni, A. Massi, Acc. Chem. Res. 39 (2006) 451.
12. P. Toto, J.C. Gesquiere, N. Cousaert, B. Deprez, N. Willand, Tetrahedron Lett. 47 (2006) 4973.
13. T. Ngouansavanh, J.P. Zhu, Angew. Chem., Int. Ed. 45 (2006) 3495.
14. J. Pospisil, T. Kumamoto, I.E. Marko, Angew. Chem., Int. Ed. 45 (2006) 3357.
15. G. Sklute, I.J. Marek, J. Am. Chem. Soc. 128 (2006) 4642.
16. A. Gazit, H. App, G. McMahon, J. Chen, A. Levitzki, F.D. Bohmer, J. Med. Chem. 39 (1996) 2170.
17. U. Sehlstedt, P. Aich, J. Bergman, E.I. Vallberg, B. Norden, A. Graslund, J. Mol. Biol. 278 (1998) 3156.
18. R.P. Trillo, Univ. Microfilms (Ann. Arbor. Mich.), L.C. card no. Mic. 59-4672, 106, Dissertation Abstr. 20 (1959) 1597.
19. S. Tries, S. Laufer, Inflammopharmacology 9 (2001) 113.
20. N.G. Argyropoulos, V.C. Sarli, M. Gdaniec, Eur. J. Org. Chem. (2006) 3738.
21. E. Borsini, G. Broggini, A. Contini, G. Zecchi, Eur. J. Org. Chem. (2008) 2808, and references cited there in.
22. H. Farsam, N. Yassa, P. Sarkhail, A. Shafiee, Planta Med. 66 (2000) 389.
23. N. Yassa, H. Farsam, A. Shafiee, A. Rustaiyan, Planta Med. 62 (1996) 583.
24. H. Farsam, N. Yassa, A. Shafiee, M. Amanlou, M. Biglar, T. Pourlotfali, Pharm. Pharmacol. Lett. 4 (1998) 79.
25. N. Yassa, H. Farsam, A. Rustaiyan, A. Shafiee, J. Sci. I.R. Iran 10 (1999) 39.
26. W.J. Lown, in: A. Padwa (Ed.), 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, Wiley, New York, 1984, p. 653.
27. R. Huisgen, A. Padwa (Eds.), 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, Wiley, New York, 1984, p. 1.
28. A. Padwa (Ed.), 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, Wiley, New York, 1984, p. 227.
29. E. Vedejs, in: D.P. Curran (Ed.), Advances in Cycloadditions, Vol. 1, JAI Press, Greenwich, CT, 1988, p. 33.
30. O. Tsuge, S. Kanemasa, Adv. Heterocycl. Chem. 45 (1989) 231.
31. A. Padwa, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1991, p. 1069.
32. P.A. Wade, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, Vol. 4, Pergamon Press, Oxford, 1991, p. 1111.
33. K.V. Gothelf, K.A. Jørgensen, Chem. Rev. 98 (1998) 863.
34. C. Najera, G.M. Curr. Org. Chem. 7 (2003) 1105.
35. J. Azizian, M.R. Mohammadizadeh, S. Zomorodbakhsh, A.A. Mohammad, A.R. Karimi, Arkivoc XV (2007) 25.
36. J. Azizian, M.R. Mohammadizadeh, S. Zomorodbakhsh, A.A. Mohammad, A.R. Karimi, Heteroatom Chem. 16 (2005) 259.
37. J. Azizian, M.R. Mohammadizadeh, A.A. Mohammad, A.R. Karimi, J. Org. Chem. 70 (2005) 350.
38. J. Azizian, A.R. Karimi, Z. Kazemizadeh, A.A. Mohammad, M.R. Mohammadizadeh, Synthesis (2005) 1095.
39. J. Azizian, A.R. Karimi, Z. Kazemizadeh, A.A. Mohammad, M.R. Mohammadizadeh, J. Org. Chem. 70 (2005) 1471.
40. J. Azizian, M.R. Mohammadizadeh, N. Karimi, Z. Kazemizadeh, A.A. Mohammad, A.R. Karimi, Heteroatom Chem. 16 (2005) 549.
41. J. Azizian, M.R. Mohammadizadeh, A.A. Mohammad, A.R. Karimi, F. Teimouri, Heteroatom Chem. 18 (2007) 16.
42. J. Azizian, A.R. Karimi, A.A. Mohammad, M.R. Mohammadizadeh, Synthesis (2004) 2263.
43. P. Allway, R. Grigg, Tetrahedron Lett. 32 (1991) 5817.
44. T. Coulter, R. Grigg, J.F. Malone, V. Sridharan, Tetrahedron Lett. 32 (1991) 5417.
45. R. Grigg, J. Idle, M. McMeekin, S. Surendrakumar, D. Vinod, J. Chem. Soc., Perkin Trans. 1 (1988) 2693.
46. R. Grigg, J. Idle, M. McMeekin, S. Surendrakumar, D. Vinod, J. Chem. Soc., Perkin Trans. 1 (1988) 2703.
47. M. Friedman, J. Agric. Food Chem. 52 (2004) 385.
48. J.L. Hallman, R.A. Bartsch, J. Org. Chem. 56 (1991) 6243.
49. D.J. McCaldin, Chem. Rev. 60 (1960) 39.
50. R. Shapiro, N. Chatterjie, J. Org. Chem. 35 (1970) 447.
51. G.H. Posner, Chem. Rev. 86 (1986) 831.
52. G. Broggini, G. Zecchi, Synthesis (1999) 905.
53. C. Najera, J.M. Sansano, Angew. Chem. Int. Ed. Engl. 44 (2005) 6272.