Synthesis and biological activity of amides and N-arylamidines of 2-alkoxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acids

Abstract

2-Alkoxy-5,6,7,8-tetrahydroquinoline-3-earboxamldes (I-VI). To a solution of sodium alc0holate prepared from 0.03 mole of sodium in 25 ml of the corresponding alcohol was added 4.2 g (0.02 mole) of 2-chloro-5,6,7,8-tetrahydroquinoline-3carboxytic acid [3] and the reaction mixture was heated in a water bath for 8-10 h. The alcohol was evaporated, the residue was washed with water, dried, and crystallized from ethanol. N-Aryl Amidines of 2-Methoxy-5,6,7,8-tetrahydroquinoline-3-carboxylic Acid (VII-X1). To an ethereal solution of arylaminodimagnesium prepared from 0.05 mole of magnesium, 0.05 mole of EtBr, and 0.025 mole of arylamine was added 4.7 g (0.025 mole) of 2-methoxy-3-cyano-5,6,7,8-tetrahydroquinoline [2] in absolute ether. The reaction mixture was heated for 3 h, and after cooling, a saturated solution of ammonium chloride was added, the ether layer was separated, washed with water to neutrality, and dried with magnesium sulfate. The ether was evaporated and the residue was crystallized from hexane or cyclohexane.