A new synthesis of chloroheterocycles via metal-halogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents

Journal of Organometallic Chemistry

Volumn 588, Issue 2, 1999, Pages 155-159

  Boga, Carla ^a   Del Vecchio, Erminia ^a   Forlani, Luciano ^a   Milanesi, Lilia ^a   Edgardo Todesco, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Aromatic heterocycles; Chlorination; Grignard reagents; Lithium compounds; Metal halogen exchange; Trichloroacetyl chloride

Indexed keywords

EID: 0041863673     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00363-0     Document Type: Article

References (18)

1. (a) J.V. Metzger, Thiazoles and their benzoderivatives, in: A.R. Katrizky, C.W. Rees (Eds.), Comprehensive Heterocyclic Chemistry, vol. 6, Pergamon, New York, 1989, pp. 235-331.
2. (b) G.V. Boyd, Oxazoles and their benzoderivatives, ibid, pp. 177-233.
3. (c) M.R. Grimmet, Imidazoles and their benzoderivatives, ibid, pp. 373-497.
4. (d) L. Forlani, P.E. Todesco, in: J.V. Metzger, A. Weissberger, E.C. Taylor (Eds.), Thiazole and its Derivatives, Wiley, New York, 1979 (Chapter 5).
5. Gschwend H.W., Rodriguez H.R. Org. React. 26:1979;1.
6. B.J. Wakefield, Compounds of the alkali and alkaline earth metals, organic synthesis, in: S.G. Wilkinson, G.A. Stone, E.W. Abel (Eds.), Comprehensive Organometallic Chemistry, Pergamon, New York, 1982, pp. 75-76 (Chapter 44).
7. (a) J. Villieras, B. Castro, Bull. Soc. Chim. Fr. (1970) 1189.
8. (b) J. Villieras, B. Castro, Bull. Soc. Chim. Fr. (1968) 246.
9. (c) H. Normant, J. Organomet. Chem. 100 (1975) 189.
10. Pinkerton F.H., Thames S.F. J. Heterocycl. Chem. 9:1971;725.
11. Kirk K.L. J. Org. Chem. 43:1978;4381.
12. Hilf C., Bosold F., Harms C., Marsch M., Boche G. Chem. Ber. 130:1997;1213. and references cited therein.
13. Bergbreiter D.E., Pendergrass E. J. Org. Chem. 46:1981;219.
14. J. Metzger, B. Koether, Bull. Soc. Chim. Fr. (1953) 702.
15. Jutzi P., Hoffmann H.-J. Chem. Ber. 106:1973;594.
16. Dondoni A., Fantin G., Fogagnolo M., Medici A., Pedrini P. J. Org. Chem. 53:1988;1748.
17. R. Bernardi, T. Caronna, R. Galli, F. Minisci, M. Perchinunno, Tetrahedron Lett. (1973) 645.
18. D. Harrison, J.T. Ralph, A.C.B. Smith, J. Chem. Soc. (1963) 2930.