A facile synthesis and application of ethyl 6-(bromomethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate

作者：Li Yang^*

来源：Research on Chemical Intermediates, 2015, 41(7): 4977-4985.

DOI：10.1007/s11164-014-1581-1

• Radical bromination
• Quinoline
• N-Bromosuccinimide
• Tungsten bulb
• Williamson reaction
• Diether

Visible-light-induced radical bromination of ethyl 6-methyl-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate (1) was effectively conducted with N-bromosuccinimide using a 150-W tungsten bulb as an initiator, leading to the desired monobromo product ethyl 6-(bromomethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate (2) in good yield of 76 %. Using the present procedure, a 46 % improvement in yield of 2 was achieved when compared with the previous method used by us. In addition, the trace amount of byproduct was isolated and identified as ethyl 9-bromo-6-methyl-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate (3) based on H-1 nuclear magnetic resonance (NMR) spectral analysis. As an extended application of 2, a new synthesis of symmetrical 2-quinolylmethoxyphenyl-containing diethers 11a-c was achieved via Williamson reaction with some dihydroxy arenes (10a-c).

• 出版日期2015-7
• 单位渤海大学