Naphthalene-catalysed Lithiation of Chlorinated Nitrogenated Aromatic Heterocycles and Reaction with Electrophiles

Author:

Gómez Inmaculada,Alonso Emma,Ramón Diego J,Yus Miguel

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference43 articles.

1. See, for instance: Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles; Thieme, G., Ed.; Verlag: Stuttgart, 1995; Chapter 6.

2. Heterocycles in Life and Society;Pozharskii,1997

3. (a) For an excellent review, see: Quéguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Adv. Heterocyclic Chem. 1991, 52, 186–303. (b) For a recent example, see: Pollet, P.; Turck, A.; Plé, N.; Quéguiner, G. J. Org. Chem. 1999, 64, 4512–4515.

4. For leading references concerning to pyridine derivatives containing a different metal of lithium, see: (a) Magnesium: Effenberger, F.; Krebs, A.; Willrett, P. Chem. Ber. 1992, 125, 1131–1140; Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359–1360; Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339–4342; Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349–1360. (b) Potassium: Verbeek, J.; Brandsma, L. J. Org. Chem. 1984, 49, 3857–3859; Pasquinet, E.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1998, 54, 8771–8782. (c) Zinc: Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 5373–5374. (d) Tin: McWhinnie, W. R.; Poller, R. C.; Thevarasa, M. J. Organometal. Chem. 1968, 11, 499–502. (e) Cerium: Shiruma, A.; Monotake, A.; Togo, H.; Yokoyama, M. Synthesis 1999, 495–499.

5. For recent examples, see: (a) Gu, Y. G.; Bayburt, E. K. Tetrahedron Lett. 1996, 37, 2565–2568. (b) Hildbrand, S.; Blaser, A.; Parel, S. P.; Leumann, C. J. J. Am. Chem. Soc. 1997, 119, 5499–5511. (c) Peterson, M. A.; Mitchell, J. R. J. Org. Chem. 1997, 62, 8237–8239. (d) Genov, M.; Kostova, K.; Dimitrov, V. Tetrahedron: Asymmetry 1997, 8, 1869–1876. (e) Corey, E. J.; Zheng, G. Z. Tetrahedron Lett. 1998, 39, 6151–6154. (f) Riedmiller, F.; Jockisch, A.; Schmidbaur, H. Organometallics 1998, 17, 4444–4453. (g) Savage, S. A.; Smith, A. P.; Fraser, C. L. J. Org. Chem. 1998, 63, 10148–10151. (h) Hannon, M. J.; Mayers, P. C.; Taylor, P. C. Tetrahedron Lett. 1998, 39, 8509–8512. (i) Uenishi, J.; Ueno, T.; Hata, S.; Nishiwaki, K.; Tanaka, T.; Wakabayashi, S.; Yonemitsu, O.; Oae, S. Heterocycles 1999, 50, 341–351.

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