397332-61-5

Upstream product

• 67462-20-8 (1R,2S)-N-amino-2-methylamino-1-phenyl-1-propanol 
• 105-58-8 Diethyl carbonate 
• 104-88-1 4-chlorobenzaldehyde 
• 612817-42-2 (5S,6R)-3-(2-methoxyacetyl)-4,5-dimethyl-3,4,5,6-tetrahydro-6-phenyl-2H-1,3,4-oxadiazin-2-one 
• 66-99-9 β-naphthaldehyde 
• 476013-32-8 (2'S,3'S,5S,6R)-3,4,5,6-tetrahydro-3-(3'-hydroxy-2'-methyl-3'-phenyl-propionyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazin-2-one 
• 1850-61-9 (1R,2S)-N-methyl-N-nitroso-2-amino-1-phenyl-1-propanol 
• 299-42-3 ephedrine 
• 620-23-5 m-tolyl aldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 612817-40-0 (5S,6R)-3,4,5,6-tetrahydro-4,5-dimethyl-3-(2-phenoxyacetyl)-6-phenyl-2H-1,3,4-oxadiazin-2-one 
• 397332-07-9 (5S,6R)-4,5-dimethyl-6-phenyl-3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 612817-41-1 (5S,6R)-3,4,5,6-tetrahydro-3-[2-(4-methoxyphenoxy)acetyl]-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazin-2-one 
• 476013-32-8 (2'S,3'S,5S,6R)-3,4,5,6-tetrahydro-3-(3'-hydroxy-2'-methyl-3'-phenyl-propionyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazin-2-one 

Relevant academic research and scientific papers

Formation of Complex Hydrazine Derivatives via Aza-Lossen Rearrangement

The development of a broadly applicable procedure for the aza-Lossen rearrangement is reported. This process converts amines into complex hydrazine derivatives in two steps under safe, mild conditions. This method allows the chemoselective formation of N-

Synthesis, X-ray crystallography and computational studies concerning an oxadiazinone derived from D-camphor: A structural limitation of oxadiazinones as chiral auxiliaries

A camphor-based oxadiazinone was prepared by reaction of the N-nitroimine of d-camphor with (1R,2S)-norephedrine; the reduction of the resultant imine; N-nitrosation of the amine; reduction to the corresponding hydrazine and cyclization. The conformationa

Oxadiazinones as chiral auxiliaries: Diastereoselective aldol addition reactions of N3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones

Asymmetric aldol reactions have been conducted with a series of N 3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine. These reactions afford the non-Evans syn-adducts in 43-97% yield and diastereoselectivities ranging from 62:38 to 99:1. Oxadiazinone substrates substituted with either the phenoxyacetyl or p-methoxyphenoxyacetyl groups gave the best results whereas the methoxyacetyl substituted oxadiazinone afforded diastereoselectivities that were modest.

An improved procedure for the asymmetric aldol reaction of the titanium enolate of an N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one

The direct formation of the titanium enolate of N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one has been achieved through complexation with titanium tetrachloride at 25°C, followed by deprotonation with triethylamine (-78 to 25°C). The preformed titanium enolate has been reacted with D2O/DCl to afford deuterated derivative 6 and also reacted with a series of aromatic and aliphatic aldehydes affording aldol adducts 4a-f with crude diastereoselectivities ranging from 8:1 to 38:1.

Toward the development of a structurally novel class of chiral auxiliaries: Diastereoselective Aldol reactions of a (1R,2S)-ephedrine-based 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one

(equation Presented) 8 examples Asymmetric aldol addition reactions have been conducted with (1R,2S)-ephedrine-derived 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (2). Diastereoselectivities range from 75:25 to 99:1 for the formation of the crude non-Evan

X-ray crystallographic and 13C nuclear magnetic resonance studies of 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from ephedrine and pseudoephedrine

3,4,5,6-Tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine have been synthesized and their conformational properties have been examined. The ephedrine heterocycles 5-7a appear to favor one set of equilibrating