2,5-Dihydro-1,3-thiazoles as Scaffolds in the Synthesis of O,N-Diacyl O,N-Acetals in a One-pot Reaction

Abstract

The Asinger reaction is a very powerful tool to form 2,5-dihydro-1,3-thiazoles in high yields. Treating these heterocyclic imines with acid chlorides followed by adding sodium carboxylates led to a large number of new O,N-diacyl O,N-acetals. Using chiral starting materials, a high diastereoselectivity was observed in several cases. X-Ray structures document the constitution and clarify the relative configuration of the prepared O, N-diacyl O,N-acetals.

Four-Component Reaction for the Synthesis of Dithiocarbamates Starting from Cyclic Imines

“…Whereas the amines were commercially available, the heterocyclic imines had to be synthesized. The imines 1 { 1 – 6 } were prepared with the help of the well-known modified Asinger 4-CR according to published procedures using an α-chloroaldehyde, a carbonyl compound (aldehyde or ketone), aqueous ammonia, and sodium hydrosulfide for the synthesis 3-thiazolines 1 { 1 – 5 } or water in case of 3-oxazoline 1 { 6 } . These types of cyclic imines are well-known for their reactivity.…”

“…These types of cyclic imines are well-known for their reactivity. The CN double bond enables multiple conversions to different type of amides, , bisamides, and polycyclic structures …”

Biocatalytic Reduction of 2‐Monosubstituted 3‐Thiazolines Using Imine Reductases

“…MS (ESI) m/z calculated for C 9 H 18 NS [M + H] + : 171.11, found: 172.00. The analytical data correspond with literature data .…”