Synthesis and Anti-juvenile Hormone Activity of 2, 2-Dimethyl-1, 2-dihydroquinoline Derivatives, Nitrogen Analogues of Precocene I and II

Abstract

A synthesis of nitrogen analogues of the natural insect anti-juvenile hormones precocene I and II is reported. The crucial step of this synthesis is thermal cyclization of the N-alkynylaniline 3 into the corresponding 1, 2-dihydroquinoline when promoted by a copper catalyst. Biological testing of the anti-juvenile hormone activity was carried out against Callosobruchus chinensis by observing the inhibition of eclosion. The 7-methoxy analogue showed higher activity than the 6, 7-dimethoxy analogue. However, the former showed lower activity than precocene I.