A one-pot access to 6-substituted phenanthridines from fluoroarenes and nitriles via 1,2-arynes

被引：76

作者：

Pawlas, J ^{[1
]}

Begtrup, M ^{[1
]}

机构：

[1] Royal Danish Sch Pharm, Dept Med Chem, DK-2100 Copenhagen, Denmark

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026197c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A one-pot, t-BuLi-induced synthesis of 6-substituted phenanthridines from fluoroarenes and nitriles via 1,2-arynes is reported. Aryl- and hetaryl nitriles, cyanamides, and trimethylacetonitrile gave phenanthridine products. The method was extended to provide bisphenanthridine 10 by a one-pot bis-cyclization, using 1,3-dicyanobenzene and PhF in 1:5 ratio. Reaction of 1-fluoronaphthalene and 4-chlorofluorobenzene with benzonitrile afforded the regioisomerically pure products 11 and 12, respectively.

引用

页码：2687 / 2690

页数：4

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