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±êÌ⣺A facile synthesis and application of ethyl 6-(bromomethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate
×÷ÕߣºYang Li
ÆÚ¿¯£ºResearch on Chemical Intermeidates
Äê·Ý£º2015
ÆÚ¾íÒ³Â룺41¾í£¬µÚ7ÆÚ£¬4977¨C4985Ò³
DOIºÅ£º10.1007/s11164-014-1581-1

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lazy½õϪ: LS-EPI+1, ¸ÐлӦÖú£¡ 2016-04-19 18:02:32
A facile synthesis and application of ethyl 6-(bromomethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate
×÷Õß:Li, Y (Li, Yang)


RESEARCH ON CHEMICAL INTERMEDIATES


¾í: 41
ÆÚ: 7
Ò³: 4977-4985
DOI: 10.1007/s11164-014-1581-1

³ö°æÄê: JUL 2015

²é¿´ÆÚ¿¯ÐÅÏ¢

RESEARCH ON CHEMICAL INTERMEDIATES  

³ö°æÉÌ SPRINGER, VAN GODEWIJCKSTRAAT 30, 3311 GZ DORDRECHT, NETHERLANDS

ISSN: 0922-6168
eISSN: 1568-5675

Ñо¿ÁìÓò Chemistry



ÕªÒª
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).

¹Ø¼ü´Ê
×÷Õ߹ؼü´Ê:Radical bromination; Quinoline; N-Bromosuccinimide; Tungsten bulb; Williamson reaction; Diether

KeyWords Plus:LEUKOTRIENE-D4 RECEPTOR ANTAGONISTS; (2-QUINOLINYLMETHOXY)PHENYL-CONTAINING COMPOUNDS; N-BROMOSUCCINIMIDE; AFFINITY; SERIES; DERIVATIVES; BROMINATION; INHIBITORS; WATER; RING

×÷ÕßÐÅÏ¢
ͨѶ×÷ÕßµØÖ·: Li, Y (ͨѶ×÷Õß)       Bohai Univ, Inst Superfine Chem, Jinzhou 121000, Peoples R China.


µØÖ·:        [ 1 ] Bohai Univ, Inst Superfine Chem, Jinzhou 121000, Peoples R China


µç×ÓÓʼþµØÖ·:bhuzh@163.com

»ù½ð×ÊÖúÖÂл
»ù½ð×ÊÖú»ú¹¹ ÊÚȨºÅ
Scientific Research Foundation of the Education Department of Liaoning Province  L2013428  
²é¿´»ù½ð×ÊÖúÐÅÏ¢¹Ø±Õ»ù½ð×ÊÖúÐÅÏ¢   

The authors would like to thank the Scientific Research Foundation of the Education Department of Liaoning Province (grant no. L2013428) for financial support.

³ö°æÉÌ
SPRINGER, VAN GODEWIJCKSTRAAT 30, 3311 GZ DORDRECHT, NETHERLANDS

Àà±ð / ·ÖÀà
Ñо¿·½Ïò:Chemistry

Web of Science Àà±ð:Chemistry, Multidisciplinary

ÎÄÏ×ÐÅÏ¢
ÎÄÏ×ÀàÐÍ:Article

ÓïÖÖ:English

Èë²ØºÅ: WOS:000356608700071

ISSN: 0922-6168

eISSN: 1568-5675

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