Solvent-free synthesis of penta-substituted pyrroles: one-pot reaction of amine, alkyl acetoacetate, and fumaryl chloride

Tetrahedron

Volumn 65, Issue 8, 2009, Pages 1704-1707

  Alizadeh, Abdolali ^a   Babaki, Mohadese ^a   Zohreh, Nasrin ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID; AMINE; CHLORIDE; FUMARYL CHLORIDE; FUNCTIONAL GROUP; HALIDE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 58249096347     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.011     Document Type: Article

References (48)

1. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1045
2. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (1998) 615
3. Nobuyoshi A., Akihiko O., Chikara M., Tatsuya T., Masami O., and Hiromitsu S. J. Med. Chem. 42 (1999) 2946
4. Baran P.S., Richter J.M., and Lin D.W. Angew. Chem., Int. Ed. 44 (2005) 609
5. Torok M., Abid M., Mhadgut S.C., and Torok B. Biochemistry 45 (2006) 5377
6. Sundberg R.J. In: Katritzky A., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 2 (1996), Pergamon, Oxford 119
7. Tao H., Hwang I., and Boger D.L. Bioorg. Med. Chem. Lett. 14 (2004) 5979
8. Baumgarten M., and Tyutyulkov N. Chem.-Eur. J. 4 (1998) 987
9. Deronzier A., and Moutet J.C. Curr. Top. Electrochem. 3 (1994) 159
10. Pagani G.A. Heterocycles 37 (1994) 2069
11. Lehuede J., Fauconneau B., Barrier L., Ourakow M., Piriou A., and Vierfond J.M. Eur. J. Med. Chem. 34 (1999) 991
12. Burli R.W., McMinn D., Kaizerman J.A., Hu W., Ge Y., Pack Q., Jiang V., Gross M., Garcia M., Tanaka R., and Moser H.E. Bioorg. Med. Chem. Lett. 14 (2004) 1253
13. Burli R.W., Jones P., McMinn D., Le Q., Duan J.X., Kaizerman J.A., Difuntorum S., and Moser H.E. Bioorg. Med. Chem. Lett. 14 (2004) 1259
14. Jonas R., Klockow M., Lues I., Pruecher H., Schliep H.J., and Wurziger H. Eur. J. Med. Chem. 28 (1993) 129
15. von der Saal W., Hoelck J.P., Kampe W., Mertens A., and Mueller-Beckmann B. J. Med. Chem. 32 (1989) 1481
16. Denny W.A., Rewcastle G.W., and Baguley B.C. J. Med. Chem. 33 (1990) 814
17. Toja E., Selva D., and Schiatti P. J. Med. Chem. 27 (1984) 610
18. Demopoulos V.J., and Rekka E. J. Pharm. Sci. 84 (1995) 79
19. Del Poeta M., Schell W.A., Dykstra C.C., Jones S., Tidwell R.R., Czarny A., Bajic M., Bajic M., Kumar A., Boykin D., and Perfect J.R. Antimicrob. Agents Chemother. 42 (1998) 2495
20. de Laszlo S.E., Visco D., Agarwal L., Chang L., Chin J., Croft G., Forsyth A., Fletcher D., Frantz B., Hacker C., Hanlon W., Harper C., Kostura M., Li B., Luell S., MacCoss M., Mantlo N., O'Neill E.A., Orevillo C., Pang M., Parsons J., Rolando A., Sahly Y., Sidler K., Widmer W.R., and O'Keefe S.J. Bioorg. Med. Chem. Lett. 8 (1998) 2689
21. Dowell R.I., Hales N.H., and Tucker H. Eur. J. Med. Chem. 28 (1993) 513
22. Ferraris D., Ficco R.P., Dain D., Ginski M., Lautar S., Lee-Wisdom K., Liang S., Lin Q., Lu M.X.C., Morgan L., Thomas B., Williams L.R., Zhang J., Zhou Y., and Kalish V.J. Bioorg. Med. Chem. 11 (2003) 3695
23. Chesworth R., Wessel M.D., Heyden L., Mangano F.M., Zawistoski M., Gegnas L., Galluzzo D., Lefker B., Cameron K.O., Tickner J., Lu B., Castleberry T.A., Petersen D.N., Brault A., Perry P., Ng O., Owen T.A., Pan L., Ke H.Z., Brown T.A., Thompson D.D., and DaSilva-Jardine P. Bioorg. Med. Chem. Lett. 24 (2005) 5562
24. Bovy P.R., Reitz D.B., Collins J.T., Chamberlain T.S., Olins G.M., Corpus V.M., McMahon E.G., Palomo M.A., Koepke J.P., Smits G.J., McGraw D.E., and Gaw J.F. J. Med. Chem. 36 (1993) 101
25. Renneberg D., and Dervan P.B. J. Am. Chem. Soc. 125 (2003) 5707
26. Marques M.A., Doss R.M., Foister S., and Dervan P.B. J. Am. Chem. Soc. 126 (2004) 10339
27. Boger D.L., Boyce C.W., Labrili M.A., Sehon C.A., and Lin Q. J. Am. Chem. Soc. 121 (1999) 54
28. Knorr L. Chem. Ber. 17 (1884) 1635
29. Paal C. Chem. Ber. 18 (1885) 367
30. Hantzsch A. Ber. Dtsch. Chem. Ges. 23 (1890) 1474
31. Berree F., Marchand E., and Morel G. Tetrahedron Lett. 33 (1992) 6155
32. Furstner A., Weintritt H., and Hupperts A. J. Org. Chem. 60 (1995) 6637
33. Katritzky A., Jiang J., and Steel P.J. J. Org. Chem. 59 (1994) 4551
34. Balme G. Angew. Chem., Int. Ed. 43 (2004) 6238
35. Nair V., Vinod A.U., and Rajesh C. J. Org. Chem. 66 (2001) 4427
36. Bharadwaj A.R., and Scheidt K.A. Org. Lett. 6 (2004) 2465
37. Tejedor D., Gonzalez-Cruz D., Garcia-Tellado F., Marrero-Tellado J.J., and Rodriguez M.L. J. Am. Chem. Soc. 126 (2004) 8390
38. Yadav J.S., Subba Reddy B.V., Rao T.S., Narender R., and Gupta M.K. J. Mol. Catal. A: Chem. 278 (2007) 42
39. Alizadeh A., Zohreh N., and Rostamnia S. Tetrahedron 63 (2007) 8083
40. Alizadeh A., and Zohreh N. Synthesis (2008) 429
41. Alizadeh A., Rostamnia S., and Hu M.L. Synlett (2006) 1592
42. Alizadeh A., Rostamnia S., Zohreh N., and Oskueyan Q. Synlett (2007) 1610
43. Alizadeh A., Movahedi F., and Esmaili A.A. Tetrahedron Lett. 47 (2006) 4469
44. Alizadeh A., Movahedi F., Masrour H., and Zhu L.G. Synthesis (2006) 3431
45. Alizadeh A., Rezvanian A., and Zhu L.G. Tetrahedron 64 (2008) 351
46. Alizadeh A., Rezvanian A., and Bijanzadeh H.R. Synthesis 5 (2008) 725
47. Bruneau C., Kaur Vohra R., and Renaud J.L. Synthesis (2007) 731
48. Motherwell W.B., Gray P.J., and Whiteheadb A.J. Synlett (2007) 431