Synthesis and reactions of 3- and 8-ethynyl-1-azaazulenes

Synthesis and reactions of 3- and 8-ethynyl-1-azaazulenes

Creators Fujii Hiroyuki

Creators Abe Noritaka

Creators Umeda Noritaka

Creators Kakehi Akikazu

3-iodo-1-azaazulenes were easily ethynylated by Sonogashira-Hagihara reaction to give 3-ethynyl-1-azaazulenes. Cyclization of 2-amino-3-ethynyl-1-azaazulene was achieved by heating in the presence of copper(II) acetate or copper(II) trifluoromethanesulfonate, and 1,9-diaza-1H-cyclopent[a]azulene derivatives were obrained. Reaction of 2-chloro-1-azaazulene with lithium phenylacetylide gave 3-chloro-1-(2-chloro-1-azaazulen-8-yl)-2-phenyl-2a-aza-2H-cyclopent[cd]azulene together with 2-chloro-8-phenylethynyl-1-azaazulene.

[ISSN]0385-5414

[NCID]AA00663739