A palladium- and copper-free cross-coupling of ethyl 3-halo-2-propynoates with 4,5,6,7-tetrahydroindoles on alumina

Tetrahedron Letters

Volumn 48, Issue 27, 2007, Pages 4661-4664

  Trofimov, B A ^a   Sobenina, L N ^a   Demenev, A P ^b   Stepanova, Z V ^a   Petrova, O V ^a   Ushakov, I A ^a   Mikhaleva, A I ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF WINDSOR   (Canada)

Author keywords

4,5,6,7 Tetrahydroindole 2 propynoates; 4,5,6,7 Tetrahydroindoles; Alumina; Cross coupling; Ethyl 3,3 di(4,5,6,7 tetrahydro 1H indol 2 yl)acrylates; Ethyl 3 halo 2 propynoates; Pyrroles

Indexed keywords

4,5,6,7 TETRAHYDROINDOLE 2 PROPYNOIC ACID DERIVATIVE; 4,5,6,7 TETRAHYDROINDOLE DERIVATIVE; [ETHYL 3,3 DI(4,5,6,7 TETRAHYDRO 1H INDOL 2 YL)ACRYLIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; ALUMINUM; COPPER; ETHYL 3 HALO 2 PROPYNOIC ACID DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; HEATING;

EID: 34249874351     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.027     Document Type: Article

References (37)

1. Jones R.A. Pyrroles (1990), Wiley, New York Part 2
2. Gribble G.W. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 2 (1996), Pergamon, Oxford 207-258
3. Sundberg R.J. Indoles (1996), Academic Press, London
4. Katritzky A.R., and Pozharskii A.F. Handbook of Heterocyclic Chemistry (2000), Pergamon Press, Oxford Chapter 4
5. Joule J.A. In: Thomas E.J. (Ed). Science of Synthesis (Houben-Weyl. Methods of Molecular Transformations) Vol. 10 (2000), Georg Thieme, Stuttgart 361-652
6. Passarella D., Giardini A., Martinelli M., and Silvani A. J. Chem. Soc., Perkin Trans. 1 (2001) 127-129
7. Hibino S., and Choshi T. Nat. Prod. Rep. 19 (2002) 148-180
8. Södenberg B.C.G. Coord. Chem. Rev. 241 (2003) 147-247
9. Beccalli E.M., Marchesini A., and Pilati T. Tetrahedron 50 (1994) 12697-12712
10. Passarella D., Lesma G., Deleo M., Martinelli M., and Silvani A. J. Chem. Soc., Perkin Trans. 1 (1999) 2669-2670
11. Giacobbe S.A., Di Fabio R., Baraldi D., Cugola A., and Donati D. Synth. Commun. 29 (1999) 3125-3135
12. Hewkin Ch.T., Di Fabio R., Conti N., Cugola A., Gastaldi P., Micheli F., and Quaglia A.M. Archiv Pharmazie 332 (1999) 55-58
13. Cho D.H., Lee J.H., and Kim B.H. J. Org. Chem. 64 (1999) 8048-8050
14. Miyaji H., Sato W., Sessler J.L., and Lynch V.M. Tetrahedron Lett. 41 (2000) 1369-1373
15. Witulski B., Azcon J.R., Alayrac C., Arnautu A., Collot V., and Rault S. Synthesis (2005) 771-780
16. Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., and Ushakov I.A. Tetrahedron Lett. 45 (2004) 6513-6516
17. Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Ushakov I.A., Elokhina V.N., Voronov V.K., and Trofimov B.A. Synthesis (2004) 2736-2742
18. Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Sinegovskaya L.M., Potekhin K.A., and Fedyanin I.V. Mendeleev Commun. 15 (2005) 229-232
19. Trofimov B.A., Sobenina L.N., Stepanova Z.V., Demenev A.P., Mikhaleva A.I., Ushakov I.A., Vakul'skaya T.I., and Petrova O.V. Zh. Org. Khim. 42 (2006) 1348-1355
20. Sobenina L.N., Demenev A.P., Mikhaleva A.I., Ushakov I.A., Vasil'tsov A.M., Ivanov A.V., and Trofimov B.A. Tetrahedron Lett. 47 (2006) 7139-7141
21. Okamoto S., Ono N., Tani K., Yoshida Y., and Sato F. J. Chem. Soc., Chem. Commun. (1994) 279-280
22. Poulsen T.B., Bernardi L., Aleman J., Overgaard J., and Jorgensen K.A. J. Am. Chem. Soc. 129 (2007) 441-449
23. Lim S., Jabin I., and Revial G. Tetrahedron Lett. 40 (1999) 4177-4180
24. Nakagawa, T.; Kawada, A. Jpn. Kokai Tokkyo Koho 2004; JP 2004010601: Chem. Absr. 2004, 140, 93921.
25. Kuehne M.E., Podhorez D.E., Mulamba T., and Bornmann W.G. J. Org. Chem. 52 (1987) 347-353
26. Hashimoto C., and Husson H.-P. Tetrahedron Lett. 29 (1988) 4563-4566
27. Modi S.P., Zayed A.-H., and Archer S. J. Org. Chem. 54 (1989) 3084-3087
28. Katritzky A.R., Li J., and Stevens C.V. J. Org. Chem. 60 (1995) 3401-3404
29. Laronze M., and Sapi J. Tetrahedron Lett. 43 (2002) 7925-7928
30. Sumi S., Matsumoto K., Tokuyama H., and Fukuyama T. Tetrahedron 59 (2003) 8571-8587
31. Cadvar H., and Saracoglu N. J. Org. Chem. 71 (2006) 7793-7799
32. 2: C, 74.53; H, 7.74; N, 8.28. Found: C, 74.37; H, 7.64; N, 8.15.
33. 3, eluent-n-hexane) to yield di(indolyl)acrylate 5 (79%).
34. 2-4), 13.6 (Me). IR (KBr) ν 3423 (NH), 1734 (C{double bond, long}O).
35. Trofimov B.A., Sobenina L.N., Stepanova Z.V., Ushakov I.A., Petrova O.V., Tarasova O.A., Volkova E.A., and Mikhaleva A.I. Synthesis (2007) 447-451
36. 2: C, 74.05; H, 7.04; N, 5.76. Found: C, 74.26; H, 7.04; N, 5.90.
37. 2: C, 76.89; H, 7.74; N, 7.17. Found: C, 76.56; H, 7.61; N, 7.31.