Coupling-isomerization-Stetter and coupling-isomerization-Stetter-Paal- Knorr sequences - A multicomponent approach to furans and pyrroles

Synthesis

Volumn , Issue 14, 2004, Pages 2391-2406

  Braun, Roland U ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Catalysis; Cross couplings; Diketones; Furans; Pyrroles

Indexed keywords

ALDEHYDES; COUPLED CIRCUITS; FLUORESCENCE; ISOMERIZATION;

COUPLING-ISOMERIZATION; STOKES SHIFTS;

FURAN RESINS;

2 (2,5 DIPHENYL 3 FURYL) 1,3 THIAZOLE; 2 [3 (4 CYANOPHENYL) 2 (2,6 DIMETHYLHEPT 5 EN 1 YL) 5 PHENYL 1H PYRROL 1 YL]ACETAMIDE; 2 [3 (4 CYANOPHENYL) 2,5 DIPHENYL 1H PYRROL 1 YL]ETHYL ACETATE; 4 (1 BENZYL 2,5 DIPHENYL 1H PYRROL 3 YL)BENZONITRILE; 4 (1 ISOPROPYL 2 PENTYL 5 PHENYL 1H PYRROL 3 YL)BENZONITRILE; 4 (2 PENTYL 5 PHENYL 1H PYRROL 3 YL)BENZONITRILE; 4 (2 PENTYL 5 PHENYL 3 FURYL)BENZONITRILE; 4 (2,5 DIPHENYL 1H PYRROL 3 YL)BENZONITRILE; 4 (2,5 DIPHENYL 3 FURYL)BENZONITRILE; 4 (5 PHENYL 2,2' BIFURAN 3 YL)BENZONITRILE; 4 [1 BENZYL 2 (2 FURYL) 5 PHENYL 1H PYRROL 3 YL]BENZONITRILE; 4 [2 (4 FLUOROPHENYL) 5 PHENYL 1H PYRROL 3 YL]PYRIDINE; 4 [2 (4 FLUOROPHENYL) 5 PHENYL 3 FURYL]PYRIDINE; 4 [2 (4 METHOXYPHENYL) 5 PHENYL 1H PYRROL 3 YL]BENZONITRILE; 4 [2 (5 HYDROXYPENTYL) 5 PHENYL 1H PYRROL 3 YL]BENZONITRILE; ALDEHYDE; DIKETONE; ETHYL [3 (4 CYANOPHENYL) 2,5 DIPHENYL 1H PYRROL 1 YL]ACETATE; FURAN DERIVATIVE; HALIDE; PROPARGYL ALCOHOL; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; FLUORESCENCE; ISOMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 5644283378     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831192     Document Type: Article

References (47)

1. (a) Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647.
2. (b) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366.
3. (c) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
4. (d) Posner, G. H. Chem. Rev. 1986, 86, 831.
5. For recent excellent reviews on transition metal assisted sequential transformations and domino processes see e.g.: (a) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101.
6. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671.
7. (c) Negishi, E.-I.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
8. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115.
9. Kobayashi, S. Chem. Soc. Rev. 1999, 28, 1.
10. Müller, T. J. J.; Ansorge, M.; Aktah, D. Angew. Chem. Int. Ed. 2000, 39, 1253.
11. Müller, T. J. J.; Braun, R.; Ansorge, M. Org. Lett. 2000, 2, 1967.
12. Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2000, 2, 4181.
13. (a) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297.
14. (b) Müller, T. J. J.; Braun, R. PCT Int Appl., WO 2002074757, A1 20020926, 2002; Chem. Abstr. 2002, 137, 262948.
15. Yehia, N. A. M.; Polborn, K.; Müller, T. J. J. Tetrahedron Lett. 2002, 43, 6907.
16. For excellent reviews see e.g.: (a) Gossauer, A. Die Chemie der Pyrrole; Springer Verlag: Berlin, 1974.
17. (b) Gossauer, A. In Houben-Weyl Methoden der Organischen Chemie, Vol. E6a; Kreher, R., Ed.; Thieme: Stuttgart, 1994, 556.
18. (c) Gribble, G. W. In Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, 207.
19. (d) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, 119.
20. (e) Fürstner, A. Synlett 1999, 1523.
21. For an interesting review see: MacDiarmid, A. G. Synth. Met. 1997, 84, 27.
22. Daidone, G.; Maggio, B.; Schillaci, D. Pharmazie 1990, 45, 441.
23. (a) Almerico, A. M.; Diana, P.; Barraja, P.; Dattolo, G.; Mingoia, F.; Loi, A. G.; Scintu, F.; Milia, C.; Puddu, I.; La Colla, P. Farmaco 1998, 53, 33.
24. (b) Almerico, A. M.; Diana, P.; Barraja, P.; Dattolo, G.; Mingoia, F.; Putzolu, M.; Perra, G.; Milia, C.; Musiu, C.; Marongiu, M. E. Farmaco 1997, 52, 667.
25. (a) Kimura, T.; Kawara, A.; Nakao, A.; Ushiyama, S.; Shimozato, T.; Suzuki, K. PCT Int. Appl., WO 2000001688, A1 20000113, 2000; Chem. Abstr. 2000, 132, 93204.
26. (b) Kaiser, D. G.; Glenn, E. M. J. Pharm. Sci. 1972, 61, 1908.
27. Lehuede, J.; Fauconneau, B.; Barrier, L.; Ourakow, M.; Piriou, A.; Vierfond, J.-M. Eur. J. Med. Chem. 1999, 34, 991.
28. (a) Kawai, A.; Kawai, M.; Murata, Y.; Takada, J.; Sakakibara, M. PCT Int. Appl., WO 9802430, A1 19980122, 1998; Chem. Abstr. 1998, 128, 140613.
29. (b) De Laszlo, S. E.; Liverton, N. J.; Ponticello, G. S.; Selnick, H. G.; Mantlo, N. B. US Patent, US 5837719, A 19981117, 1998; Chem. Abstr. 1998, 130, 10663.
30. (c) De Laszlo, S. E.; Liverton, N. J.; Ponticello, G. S.; Selnick, H. G.; Mantlo, N. B. US Patent, US 5792778, A 19980811, 1998; Chem. Abstr. 1998, 729, 161495.
31. (d) DeLaszlo, S. E.; Chang, L. L.; Kim, D.; Mantlo, N. B. PCT Int. Appl., WO 9716442, A1 19970509, 1997; Chem. Abstr. 1997, 127, 50543.
32. (a) Stetter, H.; Kuhlmann, H.; Haese, W. Org. Synth. 1987, 65, 26.
33. (b) Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407.
34. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639.
35. Hesse, M.; Meier, H.; Zeeh, B. Spektroskopische Methoden in der organischen Chemie; Thieme: Stuttgart, 1991.
36. Broaddus, C. D. US Patent, US 3557005, 19710119, 1971; Chem. Abstr. 1971, 75, 142147.
37. Irie, M. Chem. Rev. 2000, 100, 1685.
38. Stryer, L. Biochemistry, 4th ed.; W. H. Freeman & Co.: New York, 1995, 444.
39. Wang, Z.; Yeung, E. S. Pure Appl. Chem. 2001, 73, 1599.
40. deSilva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
41. Valeur, B. Molecular Fluorescence; Wiley-VCH: Weinheim, 2002, 34.
42. Organikum, 14th ed.; VEB Deutscher Verlag der Wissenschaften: Berlin, 1993.
43. (a) Brandsma, L. Preparative Acetylenic Chemistry; Eisevier: Amsterdam, 1988.
44. (b) Krause, N.; Seebach, D. Chem. Ber. 1987, 120, 1845.
45. Buu-Hoi, H. J. Chem. Soc. 1951, 1834.
46. Wu, T.-C.; Mareda, J.; Gupta, Y. N.; Houk, K. N. J. Am. Chem. Soc. 1983, 105, 6996.
47. Shechter, H.; Nagajaran, M. J. Org. Chem. 1984, 49, 62.