Twisted Amide Reduction under Wolff-Kishner Conditions: Synthesis of a Benzo-1-Aza-Adamantane Derivative
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- 作者：Crystal G. Bashore ; Ivan J. Samardjiev ; Jon Bordner ; and Jotham W. Coe
- 刊名：Journal of the American Chemical Society
- 出版年：2003
- 出版时间：March 19, 2003
- 年：2003
- 卷：125
- 期：11
- 页码：3268 - 3272
- 全文大小：133K
- 年卷期：v.125,no.11(March 19, 2003)
- ISSN：1520-5126
文摘
A synthesis of 4,5-benzo-1-aza-tricyclo[4.3.1.13,8]undecane (1), a benzo-1-aza-adamantanederivative, is described and features a previously unknown application of the Wolff-Kishner reduction ofa nonresonance stabilized or "twisted" amide. An intermediate amino ester is converted to a severely "twistedamide", which, when exposed to hydrazine in alcohol, provides the corresponding "twisted" amino hydrazone.Wolff-Kishner conditions (KOH/ethylene glycol, 200 
C) provide the reduced target 1 without hydrolysis toamino acid derivatives. These operations are conveniently performed in a single flask in high yield.
C) provide the reduced target 1 without hydrolysis toamino acid derivatives. These operations are conveniently performed in a single flask in high yield.