Tetrabutylammonium Iodide-Mediated One-Pot Construction of 1,3,4-Oxadiazole Derivatives with Alkyl Amide and Hydrazine

doi:10.6023/cjoc202304005

Abstract

1,3,4-Oxadiazole derivatives are a class of important bioactive molecules, showing good antibacterial, anti-inflam- matory and anticancer activities. In the present study, an efficient one-pot synthetic methodology has been developed for the construction of 1,3,4-oxadiazoles by utilizing acylhydrazine and alkylamide as reactants in the absence of alkaline or metallic catalysts. The expected 1,3,4-oxadiazole derivatives can be obtained with a maximum 85% yield for 10 h. This method has the advantages of simple operation, mild conditions, few by-products and wide range of substrates. And it can achieve gram preparation, showing good practical value. The mechanism study showed that the tautomerism of amide electron cloud, and the activity of tetrabutylammonium iodide (TBAI) and hydrazide carbonyl group played an important role in the reaction.

Key words: 1,3,4-oxadiazole, alkyl amide, arylhydrazide, tetrabutylammonium iodide (TBAI), one-pot

Cite this article

Zhixia Jing, Jianxi Du, Ping Jiang, Keyume Ablajan. Tetrabutylammonium Iodide-Mediated One-Pot Construction of 1,3,4-Oxadiazole Derivatives with Alkyl Amide and Hydrazine[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3930-3938.

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Entry	Oxidant (equiv.)	Solvent/mL	Temp/℃	Yield^b/%
1	I₂(1)	PhCH₃	100	75
2 3 4 5 6	I₂ (1) I₂ (1) I₂ (1) I₂ (1) I₂ (1)	H₂O DMSO DCE DCE CH₃CH₂OH	100 100 100 90 80	n.d n.d 78 50 n.d
7 8 9 10 11 12 13 14 15 16 17 18 19 20	K₂S₂O₈ (1) NBS (1) NCS (1) TBAI (1) — PhI(OAc)₂ (1) IBX (1) KI (1) NH₄I (1) NaI (1) TBAI (0.5) TBAI (2) TBAI (0.5) TBAI (0.5)	DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE	100 100 100 100 100 100 100 100 100 100 100 100 90 80	n.d 75 n.d 81 n.d n.d n.d n.d n.d n.d 85 79 38 n.d

Entry	Oxidant (equiv.)	Solvent/mL	Temp/℃	Yield^b/%
1	I₂(1)	PhCH₃	100	75
2 3 4 5 6	I₂ (1) I₂ (1) I₂ (1) I₂ (1) I₂ (1)	H₂O DMSO DCE DCE CH₃CH₂OH	100 100 100 90 80	n.d n.d 78 50 n.d
7 8 9 10 11 12 13 14 15 16 17 18 19 20	K₂S₂O₈ (1) NBS (1) NCS (1) TBAI (1) — PhI(OAc)₂ (1) IBX (1) KI (1) NH₄I (1) NaI (1) TBAI (0.5) TBAI (2) TBAI (0.5) TBAI (0.5)	DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE DCE	100 100 100 100 100 100 100 100 100 100 100 100 90 80	n.d 75 n.d 81 n.d n.d n.d n.d n.d n.d 85 79 38 n.d

四丁基碘化胺介导烷基酰胺与酰肼一锅法构建1,3,4-噁二唑衍生物