Issue 11, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines, via an unprecedented intramolecular electrophilic aromatic substitution†

Guillaume Mercey,a   Remi Legay,a   Jean-François Lohier,a   Jana Sopkova-de Oliveira Santos,b   Jocelyne Levillain,a   Annie-Claude Gaumonta  and  Mihaela Gulea*a  

* Corresponding authors

a Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN, Université de Caen Basse-Normandie, 6, Bd. Maréchal Juin, Caen, France
E-mail: mihaela.gulea@ensicaen.fr
Fax: 33 23145 2877
Tel: 33 23145 2898

b Laboratoire de Crystallographie, Centre d'Etudes et de Recherche sur le Médicament de Normandie, EA 4258, FR CNRS 3038 INC3M, Université de Caen Basse-Normandie, Bd. Becquerel, Caen

Abstract

A one-pot synthesis of various N-substituted 3-amino-thiochromanes from 4-benzyl-2-methyl thiazoline via a thiazolinium salt is described. The obtained 3-amino-thiochromanes are enantiopure, as their precursors derive from chiral 2-aminoalcohols. The reaction involves the formation of a disulfide, which subsequently takes part in an unprecedented intramolecular electrophilic aromatic substitution.

Graphical abstract: Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines, via an unprecedented intramolecular electrophilic aromatic substitution

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Article information

DOI
https://doi.org/10.1039/C003050C
Article type
Communication
Submitted
17 Feb 2010
Accepted
07 Apr 2010
First published
22 Apr 2010

Org. Biomol. Chem., 2010,8, 2520-2521

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Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines, via an unprecedented intramolecular electrophilic aromatic substitution

G. Mercey, R. Legay, J. Lohier, J. S. O. Santos, J. Levillain, A. Gaumont and M. Gulea, Org. Biomol. Chem., 2010, 8, 2520 DOI: 10.1039/C003050C

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