Construction of nitrogen heterocycles bearing an aminomethyl group by copper-catalyzed domino three-component coupling-cyclization.
A direct approach to 2-(aminomethyl)indoles by copper-catalyzed domino three-component coupling-cyclization of 2-ethynylanilines with a secondary amine and aldehyde has been developed. By use of a cyclic or acyclic secondary amine and aldehyde (paraformaldehyde, aliphatic or aromatic aldehydes) in the presence of 1 mol % of CuBr, 2-ethynylanilines were converted to a variety of substituted 2-(aminomethyl)indoles in good to excellent yields. Utilizing this domino reaction and C-H functionalization at the indole C-3 position, polycyclic indoles were readily synthesized. Construction of benzo[e][1,2]thiazine and indene motifs by the reaction of sulfonamide and malonate congeners is also presented.
Ohta
Yusuke
Y
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Chiba
Hiroaki
H
Oishi
Shinya
S
Fujii
Nobutaka
N
Ohno
Hiroaki
H
D000114:Acetylene / Q000031:analogs & derivatives / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D005557:Formaldehyde / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D008744:Methylamines / Q000737:chemistry*; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry; D013843:Thiazines / Q000138:chemical synthesis / Q000737:chemistry
C483919:2-ethynylaniline; D000447:Aldehydes; D000814:Aniline Compounds; D001965:Bromides; D006571:Heterocyclic Compounds; D007192:Indenes; D007211:Indoles; D008314:Malonates; D008744:Methylamines; D011108:Polymers; D013449:Sulfonamides; D013843:Thiazines; D005557:Formaldehyde; C408079:cupric bromide; C093581:indene; D003300:Copper; C030290:malonic acid; D009584:Nitrogen; D000114:Acetylene; C003043:paraform