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

Guillaume Mercey (1) , Rémi Legay (1) , Jean-François Lohier (1) , Jana Sopkova-de Oliveira Santos (2) , Jocelyne Levillain (1) , Annie-Claude Gaumont (1) , Mihaela Gulea (1)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie

A one-pot synthesis of various N-substituted 3-amino-thiochromanes from 4-benzyl-2-methyl thiazoline is described. The reaction involves the formation of a disulfide, which subsequently takes part in an unprecedented intramolecular electrophilic aromatic substitution.

Mots clés: heterochemistry; sulfur; amino; aminothiols; thiochromanes

Domaines: Chimie organique

Guillaume Mercey, Rémi Legay, Jean-François Lohier, Jana Sopkova-de Oliveira Santos, Jocelyne Levillain, et al.. Synthesis of 3- amino-thiochromanes from 4- benzyl 2-thiazolines, via an unprecedented intramolecular electrophilic aromatic substitution. Organic & Biomolecular Chemistry, 2010, 8, pp.2520-2521. ⟨10.1039/c003050c⟩. ⟨hal-00712798⟩