Efficient synthesis of aminomethylated pyrroloindoles and dipyrrolopyridines via controlled copper-catalyzed domino multicomponent coupling and bis-cyclization.
Efficient methods for the synthesis of pyrrole-fused indole derivatives via domino copper-catalyzed multicomponent coupling and bis-cyclization have been developed. The mono- or bis-aminomethylated pyrroloindoles and dipyrrolopyridines were selectively obtained in moderate to excellent yields by a controlled Mannich-type reaction-cyclization of 4,6-diethynyl-1,3-phenylenediamine or its pyridine congener with paraformaldehyde and a secondary amine. The high-yielding bis-cyclization of terminal alkynes without using Mannich-type reactions is also presented.
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Yamato
Y
Suzuki
Yusuke
Y
Ohta
Shinya
S
Oishi
Nobutaka
N
Fujii
Hiroaki
H
Ohno
D000480:Alkynes; D002384:Catalysis; D003300:Copper; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D008722:Methods; D011725:Pyridines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*
D000480:Alkynes; D007211:Indoles; D011725:Pyridines; D011758:Pyrroles; D003300:Copper