Synthesis of arene oxide and trans-dihydrodiol metabolites of quinoline

Abstract

Racemic samples of 5,6-epoxy-5,6-dihydroquinoline (2) (quinoline 5,6-oxide) and 7,8-epoxy-7,8dihydroquinoline (4) (quinoline 7,8-oxide) have been synthesised by two methods from the corresponding di hydroquinol ine precursors. trans-5,6-D i hydroqui noli ne-5,6 -diol (3) and trans-7,8dihydroquinoline-7,8-diol ( 5 ) were obtained both by multi-step synthetic routes from the corresponding dihydroquinolines and by the direct base-catalysed hydration of the corresponding arene oxides (2) and (4).Quinoline (1) is a major azapolycyclic aromatic hydrocarbon found in tobacco smoke,' urban particulates,2 and automobile exhaust^.^ The prevalence of quinoline (1) in the en~ironment,'-~ * 1 eV ca. 1.602 x J.

Total Synthesis of Siomycin A: Completion of the Total Synthesis

“…Since the intramolecular epoxide opening for the A‐ring construction was unsuccessful, we next investigated the intermolecular epoxide‐opening reaction using the model quinoline epoxide 18 15 (racemate) and L ‐Val‐OBn 19 (Bn=benzyl) in the presence of several types of Lewis acids as an epoxide activator. The relevant experimental data are shown in Table 1.…”

Stereocontrolled Synthesis of the Quinaldic Acid Macrocyclic System of Thiostrepton We thank Drs. D. H. Huang and G. Suizdak for NMR spectroscopic and mass spectrometric assistance, respectively, as well as Mike Sertic (University of California, San Diego) for experimental assistance. Financial support for this work was provided by The Skaggs Institute for Chemical Biology, the National Institutes of Health (USA), fellowships from The Skaggs Institute for Research (to M.Z. and F.Z.), and grants from Abbott

“…In contrast to these results, the more recently disclosed Katsuki catalyst 25 b 18 (1 mol %) in conjunction with NaOCl allowed selective epoxidation of 18 (74 %, 80 % de ). Introduction of the desired double bond in 19 was then effected by selective benzylic bromination (NBS/AIBN, 63 %), followed by elimination of HBr under basic conditions in toluene at 60°C to give epoxide 7 (86 %) 19…”

Study of in vitro glucuronidation of hydroxyquinolines with bovine liver microsomes

“…Quinoline was obtained from Wako Pure Chemical Industries (Osaka, Japan), 3-hydroxyquinoline from Tokyo Kasei Kogyo Co. (Tokyo, Japan), and 5-hydroxyquinoline (5OHQ), 6-hydroxyquinoline (6OHQ) and QNO from Sigma-Aldrich Chemie Gmbh (Steinheim, Germany). 5,6-dihydroquinoline-5,6-diol (Q5,6diol, a racemate) was synthesized by alkali hydrolysis of epoxide according to previous methods [10]. Some fluoroquinolines were produced as previously described [11].…”