Synthesis of 2,5-disubstituted 6-azaindoles from substituted aziridines via intramolecular cyclization.
A new and efficient preparation of pharmacologically and biologically important 2,5-disubstituted 6-azaindoles was achieved from cyclizations of aziridin-2-yl dipropargylic alcohols as adducts of two propargyl groups to ethyl 1-benzylaziridine-2-carboxylate. The sequential cyclizations include pyrrole formation and a novel base-catalyzed intramolecular acetylenic Schmidt reaction.
Department of Chemistry, Sogang University, Seoul 121-742, Korea.
Hogyu
H
Lee
Jun Hee
JH
Kim
Won Koo
WK
Lee
Jae-Hoon
JH
Jung
Hyun-Joon
HJ
Ha
D001372:Aza Compounds / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry
C504762:6-azaindole; D001372:Aza Compounds; D001388:Aziridines; D007211:Indoles; D011758:Pyrroles