REACTION OF 1-AZABICYCLO[1.1.0]BUTANE WITH ACTIVATED AMIDES

摘要

1-Azabicyclo[1.1.0]butane (ABB, 1) reacted with 3-acyl-1,3-thiazolidine-2-thiones (7,11a-m) in the presence of a catalytic amount of Mg(OTf)2 to give the corresponding2-(1-acylazetidin-3-yl)thio-1,3-thiazolines (8,12a-m). It was hypothesized that this reaction is primarily influenced by a steric bulkiness of acyl groups in 3-acyl-1,3-thiazolidine-2-thiones. Resulting compounds (8, 12k) were readily converted to thiols (13,14), and azetidine-3-thiol hydrochloride (15), which is the key intermediate of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride (4) useful for the preparation of a new oral 1 β-methylcarbapenem antibiotic L-084, was obtained quantitatively by hydrolysis of 14.