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Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

Authors :
Jiang-Shan Guo
Yan-Ping Zhu
Zhi‐Hao Shang
Zeng-Jing Li
Ji-Na Sun
Zhen-Xiao Zhang
Yuan-Yuan Sun
Wei-Zhao Weng
Source :
Tetrahedron. 76:130887
Publication Year :
2020
Publisher :
Elsevier BV, 2020.

Abstract

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

Details

ISSN :
00404020
Volume :
76
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........7036789be61f07602fcb6107076bcd60
Full Text :
https://doi.org/10.1016/j.tet.2019.130887