A novel direct N-alkenylation of nitrogen-containing heterocycles with magnesium alkylidene carbenoids

Tetrahedron Letters

Volumn 46, Issue 29, 2005, Pages 4855-4858

  Satoh, Tsuyoshi ^a   Sakurada, Jo ^a   Ogino, Yumi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Alkenylation; Magnesium alkylidene carbenoid; N Alkenylation of heterocycles; Sulfoxide; Sulfoxide magnesium exchange reaction

Indexed keywords

ALKANE DERIVATIVE; ALKENE DERIVATIVE; CARBENOID; HETEROCYCLIC COMPOUND; INDAZOLE DERIVATIVE; INDOLE; MAGNESIUM DERIVATIVE; NITROGEN; PHENOTHIAZINE; PHENOXAZINE DERIVATIVE; PHENYL ISOCYANATE; TOLUENE;

ALKYLATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION;

EID: 20444482519     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.058     Document Type: Article

References (22)

1. A. Kiyomori, J.-F. Marcoux, and S.L. Buchwald Tetrahedron Lett. 40 1999 2657
2. A. Klapars, J.C. Antilla, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 7727
3. J.C. Antilla, A. Klapars, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 11684
4. J.C. Antilla, J.M. Baskin, T.E. Barder, and S.L. Buchwald J. Org. Chem. 69 2004 5578 and the references cited therein
5. F. Brustolin, V. Castelvetro, F. Ciardelli, G. Ruggeri, and A. Colligiani J. Polym. Sci., Part A: Polym. Chem. 39 2001 253
6. P.E. Cross, R.P. Dickinson, M.J. Parry, and M.J. Randall J. Med. Chem. 29 1986 342
7. E. Wenkert, E.C. Angell, V.F. Ferreira, E.L. Michelotti, S.R. Piettre, J.-H. Sheu, and C.S. Swindell J. Org. Chem. 51 1986 2343
8. T. Koike, N. Takeuchi, M. Hagiwara, K. Yamazaki, and S. Tobinaga Heterocycles 51 1999 2687
9. D. Tzalis, C. Koradin, and P. Knochel Tetrahedron Lett. 40 1999 6193
10. A.Y. Lebedev, V.V. Izmer, D.N. Kazyul'kin, I.P. Beletskaya, and A.Z. Voskoboynikov Org. Lett. 4 2002 623
11. E. Abele, O. Dzenitis, K. Rubina, and E. Lukecics Chem. Heterocycl. Compd. 38 2002 682
12. B.A. Trofimov, O.A. Tarasova, M.A. Shemetova, A.V. Afonin, L.V. Klyba, L.V. Baikalova, and A.I. Mikhaleva Russ. J. Org. Chem. 39 2003 408
13. J. Barluenga, M.A. Fernandez, F. Aznar, and C. Valdes Chem. Commun. 2004 1400
14. T. Satoh, K. Takano, H. Ota, H. Someya, K. Matsuda, and M. Koyama Tetrahedron 54 1998 5557
15. T. Satoh, T. Sakamoto, and M. Watanabe Tetrahedron Lett. 43 2002 2043
16. T. Satoh, T. Sakamoto, M. Watanabe, and K. Takano Chem. Pharm. Bull. 51 2003 966
17. M. Watanabe, M. Nakamura, and T. Satoh Tetrahedron 61 2005 4409
18. T. Satoh, Y. Ogino, and M. Namamura Tetrahedron Lett. 45 2004 5785
19. S. Nunomoto, Y. Kawakami, and Y. Yamashita Bull. Chem. Soc. Jpn. 54 1981 2831
20. G. Cahiez, C. Chaboche, and M. Jezequel Tetrahedron 56 2000 2733
21. T. Satoh, R. Matsue, T. Fujii, and S. Morikawa Tetrahedron 57 2001 3891
22. 1H NMR-NOESY spectrum.