Synlett
DOI: 10.1055/s-0036-1590861
letter
© Georg Thieme Verlag Stuttgart · New York

Photochemistry of ortho-Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent Control

S. Chaabounia, b, c, N. M. Pinkertona, S. Abidb, C. Galaupc, S. Chassaing*a
  • aInstitut des Technologies Avancées en Sciences du Vivant (ITAV), Université de Toulouse, CNRS, UPS, 1 place Pierre Potier, 31106 Toulouse Cedex 1, France   Email: stefan.chassaing@itav.fr
  • bLaboratoire de Chimie Appliquée: HGP, Université de Sfax, Faculté des Sciences, Sfax 3000, Tunisia
  • cLaboratoire de Synthèse et Physicochimie de Molécules d’Intérêt Biologique (SPCMIB), CNRS-UMR5068, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062 Toulouse Cedex 9, France
The 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.
Further Information

Publication History

Received: 03 May 2017

Accepted after revision: 11 July 2017

Publication Date:
17 August 2017 (eFirst)

Abstract

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.

Supporting Information