Benzo-fused heterocycles and carbocycles by intramolecular SNAr and tandem SN2-SNAr reactions

被引：18

作者：

Bunce, Richard A. ^{[1
]}

Nago, Takahiro ^{[1
]}

Sonobe, Nathan ^{[1
]}

Slaughter, LeGrande M. ^{[1
]}

机构：

[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 02期

关键词：

D O I：

10.1002/jhet.5570450239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzo-fused heterocyclic and carbocyclic systems have been synthesized by intramolecular SNAr and tandem S(N)2-SNAr reactions. Treatment of 3-(2-fluoro-5-nitrophenyl)-1-propanol with sodium hydride in N,N-dimethylformamide gave 6-nitrochroman in 80% yield by an intramolecular SNAr reaction. Treatment of 2-(3-bromopropyl)-1-fluoro-4-nitrobenzene with benzylamine in NN-dimethylformamide gave 1-benzyl-6-nitrotetrahydroquinoline in 98% yield by a tandem S(N)2-SNAr reaction. Finally, in a similar process, reaction of this same bromide with dimethyl malonate under basic conditions gave 1,1-bis(methoxycarbonyl)-6-nitro-1,2,3,4-tetrahydronaphthalene in 80% yield. Further studies exploring ring size effects are also presented.

引用

页码：551 / 557

页数：7

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