I2‑Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides

I2‑Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides

A practical and transition-metal-free oxidative cyclization of acylhydrazones into 1,3,4-oxadiazoles has been developed by employing stoichiometric molecular iodine in the presence of potassium carbonate. The conditions of this cyclization reaction also work well with crude acylhydrazone substrates...

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Veröffentlicht in:Journal of organic chemistry 2013-10, Vol.78 (20), p.10337-10343
Hauptverfasser: Yu, Wenquan, Huang, Gang, Zhang, Yueteng, Liu, Hongxu, Dong, Lihong, Yu, Xuejun, Li, Yujiang, Chang, Junbiao
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container_end_page 10343
container_issue 20
container_start_page 10337
container_title Journal of organic chemistry
container_volume 78
creator Yu, Wenquan
Huang, Gang
Zhang, Yueteng
Liu, Hongxu
Dong, Lihong
Yu, Xuejun
Li, Yujiang
Chang, Junbiao
description A practical and transition-metal-free oxidative cyclization of acylhydrazones into 1,3,4-oxadiazoles has been developed by employing stoichiometric molecular iodine in the presence of potassium carbonate. The conditions of this cyclization reaction also work well with crude acylhydrazone substrates obtained from the condensation of aldehydes and hydrazides. A series of symmetrical and asymmetrical 2,5-disubstituted (aryl, alkyl, and/or vinyl) 1,3,4-oxadiazoles can be conveniently generated in an efficient and scalable fashion.
doi_str_mv 10.1021/jo401751h
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title I2‑Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides
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