Synthesis of substituted heterocyclic compounds

Details Synthesis of substituted heterocyclic compounds Synthesis of substituted heterocyclic compounds

C - Chemistry, Metallurgy

07

D

C07D 513/04 (2006.01) C07D 233/88 (2006.01) C07D 263/48 (2006.01) C07D 277/40 (2006.01) C07D 403/12 (2006.01) C07D 471/04 (2006.01) C07D 498/04 (2006.01)

Patent

CA 2524706

The invention relates to a method of synthesising heterocyclic compounds. The invention is characterised in that it consists in opening a compound having formula (I), wherein: - X represents NH, O, S or a N-p group, p being a protective group, such as Boc or Troc; - Y represents N, O, S; - Z represents NH¿2 ?or NH-p; and - R¿1? represents a C¿1?-C¿6 ?alkoxy radical, aryloxy, such as phenyloxy, or a pyrrolyl radical, said radicals being optionally substituted, or the salts thereof, and the isomers of the aforementioned compounds. Moreover, the above-mentioned opening step is performed in conditions such as to produce a heterocycle having formula (II), wherein: - X, Y and Z are as defined above; - R¿2? represents a -CH=CH-CH¿2?-NH-COR¿1? or -CH=CH-CH¿2?-NH-CO group; and R¿3? occupies one, two or three positions and represents a halogen. The invention can be used to synthesise natural products.

L'invention vise en procédé de synthèse de composés hétérocycliques, caractérisé en ce qu'il comprend l'ouverture d'un composé de formule (I) : dans laquelle, - X représente NH, O, S ou un groupe N-p, p étant un groupe protecteur tel que Boc ou Troc, - Y représente N, O, S., -Z représente NH¿2 ?ou NH-p et - R¿1? représente un radical alkoxy en C¿1?-C¿6?, aryloxy, notamment phényloxy, ou un radical pyrrollyle, ces radicaux étant éventuellement substitués, ou de leurs sels, et des isomères de ces composés, ladite étape d'ouverture étant réalisée dans des conditions conduisant à un hétérocycle de formule (II) dans laquelle, -X, Y et Z sont tels que définis ci-dessus, et - R¿2? représente un groupe -CH=CH-CH¿2?-NH-COR¿1? ou -CH=CH-CH¿2?-NH-CO, R¿3? occupant une, deux ou trois positions et représentant un halogène. Application à la synthèse de produits naturels.

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