Synthesis of Indoxylic Acid Esters by Rhodium-catalyzed Carbene N–H Insertion and Thermal Cyclization
Mark A. Honey A and Christopher J. Moody A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
B Corresponding author. Email: c.j.moody@nottingham.ac.uk
Australian Journal of Chemistry 67(9) 1211-1216 https://doi.org/10.1071/CH14116
Submitted: 5 March 2014 Accepted: 26 March 2014 Published: 8 May 2014
Abstract
Reaction between diethyl diazomalonate and a range of N-alkylanilines in the presence of a catalytic amount of rhodium(ii) acetate dimer afforded carbene N–H insertion to produce anilinomalonates in modest-to-good yields. Upon heating to a high temperature for a short time, the anilinomalonates underwent thermal cyclization to indoxylic acid esters.
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