Photochemistry of ortho-Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent ControlThe authors gratefully acknowledge the CNRS and Université Paul Sabatier-Toulouse III for financial support. This work was supported by the Agence Nationale de Recherche (ANR-13-JS07-0003-01 CiTrON-Fluo) and the CNRS. S.C. thanks the Campus France Agency and the Université de Sfax for financial support, and N.M.P. thanks the Fondation RITC and the Fondation Toulouse Cancer Santé for a post-doctoral scholarship.
Received: 03 May 2017
Accepted after revision: 11 July 2017
17 August 2017 (eFirst)
The light-promoted potential of ortho-azidocinnamoyl compounds is evaluated for heterocycle synthesis. Depending on the nature of the solvent, 2-acylated indoles were obtained under aprotic conditions, whereas the use of a protic medium led to 2-substituted quinolines. The synthetic significance of this metal-free method is that, by simply changing the solvent, the reaction outcome can be directed towards different key heterocyclic scaffolds.