ARENE OXIDES OF QUINOLINE - EPOXIDATION, N-OXIDATION AND N-METHYLATION REACTIONS

被引：10

作者：

BOYD, DR ^{[1
]}

DAVIES, RJH ^{[1
]}

HAMILTON, L ^{[1
]}

MCCULLOUGH, JJ ^{[1
]}

PORTER, HP ^{[1
]}

机构：

[1] QUEENS UNIV BELFAST,SCH BIOL & BIOCHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 09期

关键词：

D O I：

10.1039/p19910002189

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 1-oxide 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 trifluoromethanesulphonate yielded the corresponding N-methylquinolinium arene oxide salts 10 and 11.

引用

页码：2189 / 2192

页数：4

共 19 条

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