Polyine, 8. Zur Synthese von Amino‐ und Bisamino‐Vertretern des Octatetrains

TLDR: In this paper, the synthesis of Amino and Bisamino derivatives of octatetraynediamines has been studied in the context of bioinformatics, where the corresponding lithium 4-aminobutadiynides 3 with perchlorobutenyne 1, are dechlorinated by butyllithium to give the lithium 8-aminooctatetrynides 5a,b.

Abstract: Polyynes, 8. - Synthesis of Amino and Bisamino Derivatives of Octatetrayne The (7,8,8-trichloro-7-octene-1,3,5-triynyl)amines 4a,b, formed by the reaction of the corresponding lithium 4-aminobutadiynides 3 with perchlorobutenyne 1, are dechlorinated by butyllithium to give the lithium 8-aminooctatetraynides 5a,b. The latter react with chloromethyldiphenylsilane or with cyclohexanone to give the silylated and hydroxyalkylated compounds 6a,b and 7b, respectively. The unsymmetrically substituted octatetraynediamines 9a,b are obtained by treatment of the lithium compounds 5 with cyanogen bromide and by treatment of the formed bromoacetylenes 8 with piperidine or morpholine.