120917-18-2Relevant academic research and scientific papers
Arene Oxides of Quinoline: Epoxidation, N-Oxidation and N-Methylation Reactions
Boyd, Derek R.,Davies, R. Jeremy H.,Hamilton, Lynne,McCullough, John J.,Porter, H. Patricia
, p. 2189 - 2192 (2007/10/02)
trans-5,6,7,8-Diepoxy-5,6,7,8-tetrahydroquinoline 5, 5,6-epoxy-5,6-dihydroquinoline 1-oxide 3, 7,8-epoxy-7,8-dihydroquinoline 1-oxide 4 and trans-5,6,7,8-diepoxy-5,6,7,8-tetrahydroquinoline 6 have been formed by oxidation of the corresponding arene oxides of quinoline, 5,6-epoxy-5,6-dihydroquinoline 1 and 7,8-epoxy-7,8-dihydroquinoline 2.The cis-diepoxides, cis-5,6,7,8-diepoxy-5,6,7,8-tetrahydroquinoline 8 and cis-5,6,7,8-diepoxy-5,6,7,8-tetrahydroquinoline 1-oxide 9 were both obtained by a stepwise synthesis from 7,8-epoxy-7,8-dihydroquinoline 2 via the bromohydrin 7.N-Methylation of 5,6-epoxy-5,6-dihydroquinoline 1 and 7,8-epoxy-7,8-dihydroquinoline 2 with methyl trifluoromethanesulfonate yielded the corresponding N-methylquinolinium arene oxide salts 10 and 11.
Non-Enzymatic Hydration, Amine Addition, and Oxidation Reactions of Aza-arene Oxides
Boyd, Derek R.,Davies, R. Jeremy H.,Dunlop, Robert,Porter, H. Patricia,Hamilton, Lynne,McCullough, John J.
, p. 163 - 165 (2007/10/02)
The 5,6- and 7,8-arene oxides of quinoline were found to undergo unusual addition reactions with water and primary amines at ambient temperature to yield trans-dihydrodiol and trans-hydroxyamine adducts respectively; oxygen atom addition yielded N-oxide and trans-5,6,7,8-dioxide derivatives.
