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A Simple and Efficient One‐Pot Synthesis of 3‐Acylisoxazolines from Alcohols and α‐Nitro Ketones in the Presence of NaHSO 4 /SiO 2
Author(s) -
Aoyama Tadashi,
Itoh Kenichi,
Hanzawa Takuya,
Meguro Natsumi,
Osanai Miki,
Hayakawa Mamiko,
Ouchi Akihiko
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801196
Subject(s) - chemistry , nitrile , nitro , alcohol , yield (engineering) , organic chemistry , alcohol oxidation , combinatorial chemistry , materials science , metallurgy , alkyl
A simple and efficient method for the synthesis of 3‐acylisoxazolines has been developed using alcohols and α‐nitro ketones in the presence of NaHSO 4 /SiO 2 . The alcohols and α‐nitro ketones are initially converted into alkenes and nitrile oxides, respectively, and then react with one another to give 3‐acylisoxazolines. This procedure, using alcohols, gave the desired dihydroisoxazoles more effectively than the conventional procedure using alkenes as starting materials. The reaction proceeded through three pathways depending on the type of alcohol used; reactions between nitrile oxides and (I) endo and exo alkenes, (II) dimerized alkenes and (III) single alkenes. Most of the reactions proceeded efficiently and gave the corresponding 3‐acylisoxazolines in good to excellent yield.