A simple, efficient, regioselective and one-pot preparation of N-hydroxy- and N-O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic scope, applications and novel by-products

作者：Ieronimo Gabriella; Mondelli Alessandro; Tibiletti Francesco; Maspero Angelo; Palmisano Giovanni; Galli Simona; Tollari Stefano; Masciocchi Norberto; Nicholas Kenneth M; Tagliapietra Silvia; Cravotto Giancarlo; Penoni Andrea^*

来源：Tetrahedron, 2013, 69(51): 10906-10920.

DOI：10.1016/j.tet.2013.10.072

• Nitrosoarenes
• Alkynes
• Indoles
• Annulation
• N-Heterocycles

The thermal reaction between nitrosoarenes and alkynes under alkylating conditions produces N-alkoxyindoles as the major products in moderate to good yields and excellent regioselectivity. Various electrophiles are used affording different N-O-protected hydroxyindoles in a multi-component fashion. Privileged acetylenic substrates used in reactions with substituted nitrosoarenes are arylalkynes or propiolates. Potentially bioactive compounds and other classes of highly functionalizable indole products were prepared. Reactions between D-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton.

• 出版日期2013-12-23