Reaction of 1,8-diaminonaphthalene with some selected π-acceptors; prospective optically active non-linear cyanovinylated naphthalenes as well as synthesis of novel perimidin and pleiadene derivatives

Reactions of 1,8-diaminonaphthalene with some selected π-acceptors are reported herein. The reaction of the 1,8-diaminonaphthalene with 1,1,2,2-tetracyanoethylene (TCNE) and 7,7′,8,8′-tetracyanoquinodimethane (TCNQ), via different modes of cyanovinylation, yielded (2E)-2,3-bis-(8-aminonaphthalen-1-ylamino)-but-2-enedinitrile and 2-[4-(1H,3H-perimidin-2-ylidene)cyclohexa-2,5-dienylidene]malononitrile, respectively. On the other site, the reaction of the target molecule with 2-dicyanomethyleneindane-1,3-dione (CNIND), 2-(2,4,7-trinitro-9H-fluoren-9-ylidene)propane-dicarbonitrile (DTF) and 2,3-dichloro-4,5-dicyano(2,3,4,5-tetrachloro)-1,4-benzoquinones (DDQ and CHL-p) afforded perimidin and pleiadene derivatives.