91523-37-4

Upstream product

• 91523-31-8 O-methyl N-chloro-3-phenylpropanohydroxamate 
• 141273-91-8 methyl 3-(2-iodophenyl)propanoate 
• 591-50-4 iodobenzene 
• 1402345-89-4 3-(2-iodophenyl)-N-methoxypropanamide 
• 66191-86-4 3-(2-bromophenyl)propanoic acid,methyl ester 
• 15115-58-9 3-(2-bromophenyl)propionic acid 
• 96606-95-0 3-(2-iodophenyl)propanoic acid 

Downstream Products

• 19358-40-8 6-chloro-1,2,3,4-tetrahydroquinolin-2-one 
• 54197-66-9 3,4-dihydro-6-hydroxy-2(1H)-quinolinone 
• 119729-98-5 8-chloro-3,4-dihydro-6-hydroxycarbostyril 
• 152189-75-8 N-(2-hydroxyphenyl)-3-phenylpropanamide 
• 54197-64-7 6-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling of O -alkyl hydroxamates with aryl iodides

N-Aryl-O-alkylhydroxamic acid derivatives were prepared by copper-catalyzed cross-coupling of hydroxamates with aryl iodides. The reaction conditions are compatible with standard hydroxy-protecting groups on the hydroxylamine moiety and are applicable to

N-ALKOXY-N-ACYLNITRENIUM IONS IN INTRAMOLECULAR AROMATIC ADDITION REACTIONS

N-alkoxy-N-acylnitrenium ions are generated by treatment of N-alkoxy-N-chloroamides with silver ions in ethereal solvents.These intermediates readily cyclise onto aromatic nuclei on alkoxy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ε benzolactams.Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side-chain aromatic rings.The yields and regioselectivities of these reactions have been ascribed to different transition structures for cyclisation onto the acyl and alkoxy side-chains which involve respectively an exocyclic and endocyclic N-O ?-bond.Evidence for this exeptionally high ?-bond character has been obtained from MNDO calculations which predict a ?-bond order of 0.9 and a rotational barrier of 29.7 kcalmol-1