Approach to thiazole-containing tetrahydropyridines via Aza–Rauhut–Currier reaction and their potent fungicidal and insecticidal activity

Abstract

A convenient and efficient synthesis of multi-substituted thiazole-containing tetrahydropyridine moieties was reported using the phosphine-catalyzed Aza–Rauhut–Currier reaction with excellent yields and diastereoselectivity. Thiazole-containing tetrahydropyridines were further transformed into the corresponding piperidine derivatives. The biological activity of the title compounds was explored; they exhibited moderate insecticidal activity against Aphis laburni Kaltenbach at 100 μg mL. A 3D QSAR model accurately predicted the insecticidal activity of the structurally diverse set of test compounds. Thiazole-containing tetrahydropyridines were active against normal fungi and also had good activity against resistant fungi mutations without cross resistance; thus, these compounds will be valuable for resistance management. The predicted potential fungicidal target of the title compounds is fumarate reductase.