Journal of Organic Chemistry 2009-09-18

Construction of nitrogen heterocycles bearing an aminomethyl group by copper-catalyzed domino three-component coupling-cyclization.

Yusuke Ohta, Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

Index: J. Org. Chem. 74(18) , 7052-8, (2009)

Full Text: HTML

Abstract

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.

Related Compounds

  • Cupric bromide
  • Indene

Related Articles:

A New Hyaluronic Acid Derivative Obtained from Atom Transfer Radical Polymerization as a siRNA Vector for CD44 Receptor Tumor Targeting.

2015-11-01

[Macromol. Biosci. 15 , 1605-15, (2015)]

First multi-reactive dextran-based inisurf for atom transfer radical polymerization in miniemulsion.

2015-10-05

[Carbohydr. Polym. 130 , 141-8, (2015)]

Polymeric nanocarriers for siRNA delivery to murine macrophages.

2014-08-01

[Macromol. Biosci. 14(8) , 1096-105, (2014)]

Stretching of collapsed polymers causes an enhanced dissipative response of PNIPAM brushes near their LCST.

2015-11-21

[Soft Matter 11 , 8508-16, (2015)]

A novel pyrazole biscoumarin based chemosensors for the selective detection of Cu(2+) and Zn(2+) ions.

2015-09-05

[Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 148 , 184-8, (2015)]

More Articles...