Process for the production of 4,5,6,7-tetrahydrothieno-[3,2-C]-p

Details Process for the production of 4,5,6,7-tetrahydrothieno-[3,2-C]-p Process for the production of 4,5,6,7-tetrahydrothieno-[3,2-C]-p

1989-09-20

1990-10-23

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D47102

Patent

active

049653598

ABSTRACT:
A process for the production of 4,5,6,7-tetrahydrothieno-[3,2-c]-pyridines of the formula: ##STR1## Thus, in the case of a 4-oxo-3-piperidine-3-carboxylic acid ester of the formula: ##STR2## an allyl group is introduced in the 3 position, the ester function in the 3 position is removed, the resultant compound of the formula: ##STR3## is ionized, reduced to the corresponding aldehyde of the formula: ##STR4## and with H.sub.2 S/HCl in the presence of a metal halide is cyclized to the end product. The synthesized compounds have antithrombotic action.

REFERENCES:
"Ticlopidine: A Review of its Pharmacodynamic and Pharmacolcinetic Properties, and Therapeutic Efficacy in Platelet-Dependent Disease States" by Emmanuel Saltied and Alan Ward, Drugs, vol. 34, 1987, pp. 222-262.
"Thiophene Isosters of Isoquinoline" by Salo Gronowitz and Elina Sandberg, "Arkiv for Khemi," vol. 32, No. 19, (1971), pp. 217-227.
"Piperidine Derivatives. XV. The Preparation of 1-Benzoyl-3-carbethoxy-4-piperidine. A synthetis of Guvaeine," S. M. McElwain & Gilbert Strole, Jour. of Am. Chem. Soc., vol. 68, Jan-Jun. 1946, pp. 1049 to 1053.
"Synthese Des Thienopyridines" by F. Eloy and A. Deryckere, Bulletin Des Societes Chemiques Belges, vol. 79 (1970), Mai, Juin issue, pp. 301-311.

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