The reaction of nitrones with pyrroles and furan: An easy access to heteroaromatic hydroxylamines and bis(heteroaryl)alkanes

Tetrahedron Letters

Volumn 46, Issue 50, 2005, Pages 8653-8656

  Berini, Christophe ^a   Minassian, Frédéric ^a   Pelloux Léon, Nadia ^a   Vallée, Yannick ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

2,2 Bis(heteroaryl)alkanes; Furan; Hydroxylamines; Nitrones; Pyrroles

Indexed keywords

ALKANE DERIVATIVE; AROMATIC COMPOUND; FURAN; HETEROCYCLIC COMPOUND; HYDROCHLORIC ACID; HYDROXYLAMINE; NITRONE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 27744453843     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.061     Document Type: Article

References (33)

1. B. Sayah, N. Pelloux-Léon, and Y. Vallée J. Org. Chem. 65 2000 2824 2826
2. B. Sayah, N. Pelloux-Léon, A. Milet, J. Pardillos-Guindet, and Y. Vallée J. Org. Chem. 66 2001 2522 2525
3. J. Patel, N. Pelloux-Léon, F. Minassian, and Y. Vallée J. Org. Chem. 70 2005 9081 9084
4. D.M. Ketcha G.W. Gribble T.L. Gilchrist Progress in Heterocyclic Chemistry Vol. 14 2002 Pergamon Oxford 114 121
5. Y. Sakata, Y. Hirano, H. Tatemitsu, S. Misumi, H. Ochiai, and H. Shibata Tetrahedron 45 1989 4717 4727
6. A. Srinivasan, and H. Furuta Acc. Chem. Res. 38 2005 10 20 and references cited therein
7. C. Zhang, J. Dong, T. Cheng, and R. Li Tetrahedron Lett. 42 2001 461 463 and references cited therein
8. R. Grigg, Z. Rankovic, and M. Thoroughgood Tetrahedron 56 2000 8025 8032
9. S.U. Pandya, C. Garçon, P.Y. Chavant, S. Py, and Y. Vallée Chem. Commun. 2001 1806 1807
10. S. Pinet, S.U. Pandya, P.Y. Chavant, A. Ayling, and Y. Vallée Org. Lett. 4 2002 1463 1466
11. S.K. Patel, K. Murat, S. Py, and Y. Vallée Org. Lett. 5 2003 4081 4084
12. H. Chalaye-Mauger, J.-N. Denis, M.-T. Averbuch-Pouchot, and Y. Vallée Tetrahedron 56 2000 791 804 and references cited therein
13. 3-Ethyl-2,4-dimethylpyrrole 1b was prepared by LAH-mediated reduction from commercially available compound 1a in a 81% isolated yield.
14. For the preparation of nitrones, see: for 2a:A. Dondoni, S. Franco, F. Junquera, F. Merchán, P. Merino, and T. Tejero Synth. Commun. 24 1994 2537 2550
15. for 2b:S.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, and S. Watanabe J. Org. Chem. 55 1990 1736 1744
16. See for example: Y. Sakata, Y. Hirano, H. Tatemitsu, S. Misumi, H. Ochiai, and H. Shibata Tetrahedron 45 1989 4717 4727
17. First isolation of indol-3′-ylcarbinols under acidic clay-catalyzed conditions has been recently described: M. Chakrabarty, S. Karmakar, and Y. Harigaya Heterocycles 65 2005 37 48
18. Isolable pyrrole-based carbinols have been obtained from electron deficient aldehydes: R.C. Blinn, F.A. Gunther, and R.L. Metcalf J. Am. Chem. Soc. 76 1954 37 39
19. J.E. Bishop, J.F. O'Connell, and H. Rapoport J. Org. Chem. 56 1991 5079 5091
20. Similarly to the indole series, the second pyrrole would add onto intermediate 2-alkylidene-2H-pyrrolium cations. See Ref. 7.
21. Unsymmetrical 2,2′-bis(pyrrolyl)alkanes are often prepared: from pyrroles and aldehydes using statistical approaches, sometimes requiring tedious chromatographic separation: C.-H. Lee, F. Li, K. Iwamoto, J. Dadok, A.A. Bothner-By, and J.S. Lindsey Tetrahedron 51 1995 11645 11672 and references cited therein
22. from 2-acetoxymethylpyrroles: A.H. Jackson, R.K. Pandey, K.R.N. Rao, and E. Roberts Tetrahedron Lett. 26 1985 793 796
23. J. Clayden, N. Greeves, S. Warren, and P. Wothers Organic Chemistry 2001 Oxford University Press Oxford 1157
24. H. Mayr, B. Kempf, and A.R. Ofial Acc. Chem. Res. 36 2003 66 77
25. Compound 9 was previously obtained from benzaldehyde in 33% yield and used for the syntheses of core-modified porphyrins. See: W.-S. Cho, and C.-H. Lee Bull. Korean Chem. Soc. 19 1998 314 319
26. For the preparation 2,2′-bis(furyl)alkanes or 2,2′- bis(thienyl)alkanes using aldehydes under acidic conditions and their synthetic applications, see: A. Riad, Z. Mouloungui, M. Delmas, and A. Gaset Synth. Commun. 24 1989 2571 2576
27. M. Skouta, A. Lesimple, Y. Le Bigot, and M. Delmas Synth. Commun. 24 1994 2571 2576
28. J. Ancerewicz, and P. Vogel Helv. Chim. Acta 79 1996 1393 1414
29. 2O: C, 73.01; H, 7.88; N, 12.16. Found (%): C, 72.63; H, 7.93; N, 11.98.
30. 2: C, 72.58; H, 8.33; N, 8.91. Found (%): C, 72.36; H, 8.35; N, 8.52.
31. 2: C, 72.71; H, 7.41; N, 6.06. Found (%): C, 72.53; H, 7.54; N, 5.95.
32. A. Dondoni, F. Junquera, F.L. Merchán, P. Merino, M.-C. Scherrmann, and T. Tejero J. Org. Chem. 62 1997 5484 5496
33. Alkaline 2,3,5-triphenyltetrazolium chloride gives bright red coloration with hydroxylamines. H. Metz Naturwissenchaften 48 1961 569 570