Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines, via an unprecedented intramolecular electrophilic aromatic substitution.
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.
Mercey
Guillaume
G
Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN, Université de Caen Basse-Normandie, 6, Bd. Maréchal Juin, 14050, Caen, France.
Legay
Remi
R
Lohier
Jean-François
JF
Santos
Jana Sopkova-de Oliveira
JS
Levillain
Jocelyne
J
Gaumont
Annie-Claude
AC
Gulea
Mihaela
M
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D013844:Thiazoles