1.
J Org Chem
; 66(16): 5595-600, 2001 Aug 10.
Article
in English
| MEDLINE
| ID: mdl-11485489
ABSTRACT
alpha-(Benzotriazolyl)methyl thioethers 1a-e reacted with styrenes under Lewis acid catalysis to give novel polysubstituted thiochromans (3,4-dihydro-2H-1-benzothiopyrans) 3-14 and 16-20 in generally high yields. Most thiochromans were isolated as one diastereomer following recrystallization. The configuration and conformation of the products are predicted on the basis of their NMR data. A stepwise reaction, proceeding via a [4(+) + 2] cationic polar cycloaddition mechanism, is proposed.
Subject(s)
Anti-Inflammatory Agents/chemical synthesis , Chromans/chemical synthesis , Anti-Inflammatory Agents/chemistry , Antidepressive Agents/chemical synthesis , Antidepressive Agents/chemistry , Cations/chemistry , Chromans/chemistry , Magnetic Resonance Spectroscopy , Molecular Conformation
2.