ChemInform Abstract: An Approach to Highly Functionalized Quinolines and Isoquinolines via a Gold-Catalyzed Benzannulation (original) (raw)

An Approach to Highly Functionalized Quinolines and Isoquinolines via a Gold-Catalyzed Benzannulation

Synlett, 2011

Supporting Information General. All melting points are uncorrected. 1 H NMR and 13 C NMR spectra were recorded on the Bruker-400 (400 MHz 1H, 100 MHz 13C) and Bruker-200 (200 MHz 1H, 50 MHz 13C) spectrometers in deuteriochloroform(CDCl3) with chloroform (7.26 ppm 1H, 77.2 ppm 13C) as an internal reference.. The data are reported in the following order: chemical shift in ppm(δ); multiplicity are indicated, br = broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet; coupling constants, J, are reported (Hz). Chemical Ionization (CI) mass spectra were obtained through the

New vistas in quinoline synthesis

Tetrahedron, 2007

The gold-catalyzed Friedlander reaction was applied to the condensation of 2-aminoarylketones with b-keto-esters, b-diketones, b-keto-amides, and b-keto-sulfones to afford a diverse range of 2,3,4-trisubstituted quinolines in 3-82% yield. The seven-membered rings 1,3-cycloheptadione and azepane-2,4-dione reacted smoothly in 75% yield. An alternative procedure for the synthesis of 3-(methanesulfonyl)quinolines was developed and provided an entry into late stage manipulation of the 4-position of these quinolines. The requisite 2-aminoarylketones for the Friedlander reaction were prepared in one pot by modified Sugasawa reaction using gallium(III) chloride and boron(III) chloride in 12-54% yield.