Synthesis and reactions of 1-amino-5-morpholin-4-yl-6,7,8,9- tetrahydrothieno[2,3-c]isoquinoline

Abstract

The pyrazolone derivative 4 was synthesized by reaction of carbohydrazide 2 with ethyl benzoylacetate in ethanol and p-toluene sulphonic acid followed by cyclization upon heating in acetic acid. Chloroacylation of amino ester and amino benzoyl compounds 1, 19 gave the chloro acetylamino derivatives 5 and 20 respectively which both of them react with different amines to afford compounds 6, 23a-d. Hydrolysis and decarboxlation of compound 1 yielded the aminothienotetrahydroisoquinoline 8 which was used as versatile material for synthesizing other heterocyclic compounds 9-18. Compound 20 react with hexamethylenetetramine and malononitrile yielded thediazepino and pyrrolo derivatives 21, 22 respectively.