TiCl4-Mediated Synthesis of 3,4-Hetero-Disubstituted Isocoumarins by Means of Isocyanide Insertion Reactions

Sudipta Ponra (1, 2) , Aude Nyadanu (3, 2, 4) , Sylvie Maurin (2) , Laurent El Kaim (4, 3) , Laurence Grimaud (2, 5) , Maxime Vitale (1, 5)

1 ENSCP - Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL
2 PASTEUR - Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640)
3 DCSO - Laboratoire de synthèse organique
4 ENSTA Paris - École Nationale Supérieure de Techniques Avancées
5 LBM UMR 7203 - Laboratoire des biomolécules

The isocyanide insertion into sulfanyl-phthalides under Lewis acid conditions is reported with full details. This sequential three-component reaction affords a new straightforward and highly convenient method for the preparation of 3-amino-4-sulfanyl isocoumarins, the potential of which is still unexplored.

Keywords: isocyanides; isocoumarins; thio-Passerini reaction; thiocarbonyl surrogates

Domains: Organic chemistry

Sudipta Ponra, Aude Nyadanu, Sylvie Maurin, Laurent El Kaim, Laurence Grimaud, et al.. TiCl4-Mediated Synthesis of 3,4-Hetero-Disubstituted Isocoumarins by Means of Isocyanide Insertion Reactions. Synthesis: Journal of Synthetic Organic Chemistry, 2018, 50 (06), pp.1331-1342. ⟨10.1055/s-0036-1591733⟩. ⟨hal-02095068⟩