82169-96-8

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 
• 105-13-5 4-Methoxybenzyl alcohol 
• 3717-21-3 p-methoxyl benzaldoxime 
• 123-11-5 4-methoxy-benzaldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 26218-40-6 3,4-bis(4-methoxyphenyl)-1,2,5-oxadiazole-2-oxide 

Downstream Products

• 82164-07-6 3-(4-Methoxy-phenyl)-isoxazole-4,5-dicarboxylic acid bis-benzylamide 
• 874-90-8 4-methoxybenzonitrile 

Relevant academic research and scientific papers

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.

Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides

The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone provided efficiently the corresponding diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Aromatic aldoximes are the key intermediates in both reactions, and 5-aryltetrazoles and 3-arylisoxazoles could be obtained from aryl bromides in one pot under transition-metal-free conditions.

Hypervalent iodine mediated synthesis of di- and tri-substituted isoxazoles via [3+2] cycloaddition of nitrile oxides

An efficient and rapid protocol for the synthesis of 3,4-disubstituted and 3,4,5-trisubstituted isoxazoles under catalyst-free conditions is described. This protocol involves pre-oxidation of aldoxime into nitrile oxide using diacetoxyiodobenzene. The in