15645-75-7Relevant articles and documents
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
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
, p. 10906 - 10920 (2014/01/06)
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 o-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton.
PREPARATION AND REACTIVITY OF ARYLSULFONYL SUBSTITUTED CYCLOPROPENES
Padwa, Albert,Wannamaker, M. Woods
, p. 6139 - 6156 (2007/10/02)
A study of the cycloaddition behaviuor of several arylsulfonyl substituted alkynes with 2-diazopropane has been carried out.These activated acetylenes react to give 3H-pyrazoles which extrude nitrogen on photolysis to produce cyclopropenes in high yield.Soft nucleophiles such as thiophenoxide readily add to the activated pi-bond to give thiophenyl substituted cyclopropanes.Reaction of 1-phenylsulfonyl-2,3,3-trimethylcyclopropene with n-butyllithium followed by alkylation with various electrophiles produces arylsulfonyl substituted methylene cyclopropanes.These compounds undergo thermal rearrangement to the thermodynamically more stable isopropylidene cyclopropane.