Synthesis 2018; 50(06): 1331-1342
DOI: 10.1055/s-0036-1591733
paper
© Georg Thieme Verlag Stuttgart · New York

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

Sudipta Ponra
a   Chimie ParisTech, PSL Research University, CNRS, Institut de Recherche de Chimie Paris (IRCP), 75005 Paris, France   Email: maxime.vitale@chimie-paristech.fr
c   PASTEUR, Département de Chimie, École Normale Supérieure, PSL Research University, Sorbonne Universités, UPMC Univ. Paris 06, CNRS, 75005 Paris, France   Email: laurence.grimaud@ens.fr
,
Aude Nyadanu
b   LSO (UMR 7652), École Polytechnique - ENSTA ParisTech, Université Paris-Saclay, 91120, Palaiseau, France   Email: laurent.elkaim@ensta-paristech.fr
c   PASTEUR, Département de Chimie, École Normale Supérieure, PSL Research University, Sorbonne Universités, UPMC Univ. Paris 06, CNRS, 75005 Paris, France   Email: laurence.grimaud@ens.fr
,
Sylvie Maurin
c   PASTEUR, Département de Chimie, École Normale Supérieure, PSL Research University, Sorbonne Universités, UPMC Univ. Paris 06, CNRS, 75005 Paris, France   Email: laurence.grimaud@ens.fr
,
b   LSO (UMR 7652), École Polytechnique - ENSTA ParisTech, Université Paris-Saclay, 91120, Palaiseau, France   Email: laurent.elkaim@ensta-paristech.fr
,
c   PASTEUR, Département de Chimie, École Normale Supérieure, PSL Research University, Sorbonne Universités, UPMC Univ. Paris 06, CNRS, 75005 Paris, France   Email: laurence.grimaud@ens.fr
,
Maxime R. Vitale*
a   Chimie ParisTech, PSL Research University, CNRS, Institut de Recherche de Chimie Paris (IRCP), 75005 Paris, France   Email: maxime.vitale@chimie-paristech.fr
› Author Affiliations
This work has been supported by IDEX, referenced as «ANR-10-IDEX-0001-02 PSL.
Further Information

Publication History

Received: 11 October 2017

Accepted after revision: 07 November 2017

Publication Date:
13 December 2017 (online)


Abstract

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.

Supporting Information

 
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