通过亚硝基芳烃与炔烃的烷基化环加成高效合成N-甲氧基吲哚。

Efficient synthesis of N-methoxyindoles via alkylative cycloaddition of nitrosoarenes with alkynes.

作者信息

Penoni Andrea, Palmisano Giovanni, Broggini Gianluigi, Kadowaki Ayako, Nicholas Kenneth M

机构信息

Dipartimento di Scienze Chimiche ed Ambientali, Università degli Studi dell'Insubria, via Valleggio 11, 22100, Como, Italy.

出版信息

J Org Chem. 2006 Jan 20;71(2):823-5. doi: 10.1021/jo051609r.

DOI:10.1021/jo051609r

PMID:16409003

Abstract

[reaction: see text] N-Methoxyindoles are produced in moderate to excellent yields from the reaction between nitrosoarenes and alkynes in the presence of K2CO3/(CH3)2SO4. Terminal alkynes with conjugating substituents afford 3-substituted N-methoxyindoles exclusively. The analogous reactions with methyl propiolate provide a one-step preparation of phytoalexin analogues from Wasabi.

摘要

[反应：见正文] 在碳酸钾/硫酸二甲酯存在下，亚硝基芳烃与炔烃反应可中等至优异产率地生成N-甲氧基吲哚。带有共轭取代基的末端炔烃仅生成3-取代的N-甲氧基吲哚。与丙酸甲酯的类似反应提供了一种从芥末一步制备植物抗毒素类似物的方法。