Donald B. Harden

Regioselective additions of grignard and lithium reagents to 2-[(benzylidene)aminoi]benzonitrile and 2-[(diphenylmethylene)amino]benzonitrile

Abstract Phenylmagnesium bromide and methylmagnesium bromide in tetrahydrofuran undergo a regioselective addition to the cyano group of the two title compounds. Phenyllithium and methyllithium add selectively to the azomethine portion of 2-[(benzylidene)amino]benzonitrile, but to the cyano group of 2-[(diphenylmethylene)amino]benzonitrile. These addition reactions are utilized in the synthesis of quinazoline derivatives.

A Novel Route to 7-(Substituted Amino)-5,6-dihydrobenz[c]acridines

The title compounds (3) are produced in a novel, lithium alkylamide- and dialkylamide-mediated cyclization of N-(1,2,3,4-tetrahydro-1-naphthylidene)-2-trifluoromethylaniline (2). The mechanism of this unusual transformation that involves the trifluoromethyl group is discussed

Highly stereoselective rearrangement of (E,E)-suspensolide to anastrephin and epianastrephin

Abstract The facility of the title rearrangement has clear mechanistic implications for the major pathway in the biosynthetic production of anastrephin ( 2 ) and epianastrephin ( 3 ) in the male Anastrepha fruit fly species A. suspensa (Caribbean) and A. ludens (Mexican).

Conformational analysis of 4,8-dimethyl-3(E),8(E)-decadien-10-olide (E,E-suspensolide), a key component of the pheromones of the male caribbean and mexican fruit flies

Abstract Molecular modeling and NMR studies of suspensolide (1), a major component of the sex and aggregation pheromones of the Caribbean, A. suspensa [Loew], and Mexican, A. ludens [Loew], fruit flies reveal two major conformers with the methyls syn.

Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides

Abstract Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiffs bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta -substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.