Experimental and theoretical investigation of the coarctate cyclization of (2-ethynylphenyl)phenyldiazenes

被引：54

作者：

Shirtcliff, LD

Weakley, TJR

Haley, MM ^{[1
]}

Köhler, F

Herges, R

机构：

[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA

[2] Univ Kiel, Inst Organ Chem, D-24098 Kiel, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 21期

关键词：

D O I：

10.1021/jo049011r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to substituted 2-phenyl-2H-indazoIes through the cyclization of (2-ethynylphenyl)-phenyldiazenes is presented. A coarctate reaction pathway forms the isoindazole carbene under neutral conditions, at moderate temperatures, and without the requirement of a carbene stabilizer. A wide variety of previously unknown diazene precursors was synthesized and cyclized. Trapping of the carbene with a silyl alcohol followed by deprotection affords the 3-hydroxymethyl-2-phenyl-2H-indazoles in good overall yield. The free carbene could also be trapped as a [2 + 1] cycloadduct with 2,3-dimethyl-2-butene.

引用

页码：6979 / 6985

页数：7

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