| 摘要 |
R1-substd.-2- or 3-thienyl-CHR2-CHR3-NH-CHR4-Ar derivs. of formula (I) are prepd by (a) condensation of a phosphonate, phosphinate, phosphene oxide or phosphonamide deriv. of formula XYP(O)-CHR3-NH2 (II), with a carbonyl cpd. Ar-CO-R4 (III) to form XYP(O)-CHR3-N=CR4-Ar (IV); (b) treatment of (IV) with a base B(-)M(+) to form the carbanion XYP(O)-CR3M(+)-N=CR4-Ar (V); (c) (V) is reacted with a thiophene-carbonyl cpd. R1-thienyl-CO-R2 (VII) to form R1-thienyl-CR2=CR3-N=CR4-Ar (VIII) which is reduced to yield (I) (where R1 in posn. 2, 3, 4 or 5 is H, halo, nitro, carboxy, cyano, amino, opt. branched alkyl, opt. branched alkoxy, aryl or aromatic heterocyclic (opt. mono- or poly-substd. by halo, nitro, cyano, amino, carboxy, alkyl, alkoxy or phenyl). The amino-ethyl side chain is joined to the thiophene ring at posns. 2 or 3; R2, R3, R4 are H, aryl or aromatic heterocyclic (opt. mono- or poly-substd. by halo, nitro, cyano, amino, carboxy, alkyl, alkoxy or phenyl); Ar is aryl or aromatic heterocyclic (opt. mono- or poly-substd. by alkyl, phenyl, halo, nitro, cyano, amino, carboxy or alkoxy); X, Y independently are alkyl, alkoxy, aryl, aryloxy, dialkyl or diaryl-amino. The base B-M+ may be an alkali metal hydride, amide or alkylamide, an organometallic cpd. e.g. n-butyllithium or an alkali metal or alkaline earth alcoholate or hydroxide. Some of cpds. (I) are new. (I) are chemical and pharmaceutical intermediates e.g. for tetrahydrothieno(3,2-c)pyridines and thieno(2,3-c)pyridines, which have therapeutic use (see French applicn. 73.03503, 75.03968, 75.20241, 75.23788, 75.24486, 76.00003 and 77.21517). |
