98057-92-2

Upstream product

• 3196-23-4 methyl 1-bromocyclohexanecarboxylate 
• 100-52-7 benzaldehyde 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 16673-80-6 6-methyl-2-phenyl-4H-1,3-oxazin-4-one 
• 455-32-3 benzoyl fluoride 
• 40195-26-4 1-methoxy-1-trimethylsilyloxymethylenecyclohexane 
• 98-88-4 benzoyl chloride 
• 93-89-0 benzoic acid ethyl ester 
• 98057-71-7 2-(1-methoxycarbonylcyclohexan-1-yl)-6-methyl-2-phenyl-3,4-dihydro-2H-1,3-oxazin-4-one 

Downstream Products

• 855428-40-9 C₁₄H₁₆O₃ 

Relevant academic research and scientific papers

Radical N-heterocyclic carbene catalysis for β-ketocarbonyl synthesis

N-Heterocyclic carbene-catalyzed radical cross-coupling between aldehydes and α-bromoesters or α-bromoamides is described. β-Ketocarbonyl compounds having a quaternary carbon center at the α-position can be synthesized under mild reaction conditions. Both aromatic and aliphatic aldehydes are suitable acyl donors by employing proper NHC catalyst precursors.

DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride

A mild and efficient transprotection of alcohols from silyl ethers 1a-f to benzoates 2a-f is reported in fair to good yields (50-98%). This silyl-acyl exchange reaction proceeds readily in acetonitrile at room temperature in the presence of benzoyl fluoride and DMAP as an acyl transfer catalyst. A two-step 'one-pot' DMAP-catalyzed silylcyanation-transprotection sequence which gives the corresponding O-benzoyl cyanohydrines 2g-l in high yields (72-98%) from various benzaldehyde and ketone derivatives is also reported. This original organocatalytic acyl transfer process was also found to be effective in the O-benzoylation of trimethysilyl enolates 1m-o, providing enol esters 2m-o. Lastly, the potential of this strategy is also illustrated by a DMAP-mediated Claisen condensation between ketene silyl acetals 1p-r and benzoyl fluoride. Georg Thieme Verlag Stuttgart.

REACTION OF SILYLKETENE ACETALS WITH ACRYLOYL AND MONO SUBSTITUTED ACRYLOYL CHLORIDES.

The reaction of silylketene acetals with acryloyl, methacryloyl and crotonyl chlorides gave, after addition of methanol, mainly substituted glutaric esters, probably via a cycloaddition.

1,3-Oxazines and Related Compounds. X. Ring Transformation of 1,3-Oxazin-4-ones into Pyridine Derivatives

Ring transformations of 2-aryl-6-methyl-4H-1,3-oxazin-4-ones (1-3) with carbanions derived from various ketones, esters, lactones and nitriles to give 3-acetyl-4,5,6-trisubstituted-2-pyridone derivatives 12 were explored. 1,3-Oxazin-4-ones (1-3) underwent