Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent: Facile synthesis of 1,2,4-oxadiazole-3-carboxamide

Shaoqing Du; Jin Li; Wen Fu; Xiaoyong Xu; Xusheng Shao; Xuhong Qian

doi:10.1016/j.tetlet.2021.153209

Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent: Facile synthesis of 1,2,4-oxadiazole-3-carboxamide

Shaoqing Du
, Jin Li
, Wen Fu
, Xiaoyong Xu
, Xusheng Shao^*
, Xuhong Qian

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China University of Science and Technology

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

1,2,4-Oxadiazole-3-carboxamide has been extensively used in the pharmaceutical chemistry. In this study, 1,2,4-oxadiazole-3-carboxamide is accomplished through an acid-promoted reaction of N-(cyanomethyl)amide with nitrosation reagent. This novel preparation of 1,2,4-oxadiazole-3-carboxamide was carried out at 25 °C, and the yield of target compounds was as high as 92%. At the same time, the amount of acid used is reduced. A mechanism speculation for the formation of 1,2,4-oxadiazole-3-carboxamide has been provided. The new synthetic method provides great convenience for the synthesis of compounds containing 1,2,4-oxadiazole-3-carboxamide.

Original language	English
Article number	153209
Journal	Tetrahedron Letters
Volume	76
DOIs	https://doi.org/10.1016/j.tetlet.2021.153209
State	Published - 20 Jul 2021

Keywords

1,2,4-Oxadiazole-3-carboxamide
Methyl 1,2,4-oxadiazole-3-carboxylate
N-(Cyanomethyl)amide
N′-Hydroxycarbamimidoyl cyanide

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10.1016/j.tetlet.2021.153209

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@article{3257742963ed4b0e93632dcbe37879a7,

title = "Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent: Facile synthesis of 1,2,4-oxadiazole-3-carboxamide",

abstract = "1,2,4-Oxadiazole-3-carboxamide has been extensively used in the pharmaceutical chemistry. In this study, 1,2,4-oxadiazole-3-carboxamide is accomplished through an acid-promoted reaction of N-(cyanomethyl)amide with nitrosation reagent. This novel preparation of 1,2,4-oxadiazole-3-carboxamide was carried out at 25 °C, and the yield of target compounds was as high as 92\%. At the same time, the amount of acid used is reduced. A mechanism speculation for the formation of 1,2,4-oxadiazole-3-carboxamide has been provided. The new synthetic method provides great convenience for the synthesis of compounds containing 1,2,4-oxadiazole-3-carboxamide.",

keywords = "1,2,4-Oxadiazole-3-carboxamide, Methyl 1,2,4-oxadiazole-3-carboxylate, N-(Cyanomethyl)amide, N′-Hydroxycarbamimidoyl cyanide",

author = "Shaoqing Du and Jin Li and Wen Fu and Xiaoyong Xu and Xusheng Shao and Xuhong Qian",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = jul,

day = "20",

doi = "10.1016/j.tetlet.2021.153209",

language = "英语",

volume = "76",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent

T2 - Facile synthesis of 1,2,4-oxadiazole-3-carboxamide

AU - Du, Shaoqing

AU - Li, Jin

AU - Fu, Wen

AU - Xu, Xiaoyong

AU - Shao, Xusheng

AU - Qian, Xuhong

PY - 2021/7/20

Y1 - 2021/7/20

N2 - 1,2,4-Oxadiazole-3-carboxamide has been extensively used in the pharmaceutical chemistry. In this study, 1,2,4-oxadiazole-3-carboxamide is accomplished through an acid-promoted reaction of N-(cyanomethyl)amide with nitrosation reagent. This novel preparation of 1,2,4-oxadiazole-3-carboxamide was carried out at 25 °C, and the yield of target compounds was as high as 92%. At the same time, the amount of acid used is reduced. A mechanism speculation for the formation of 1,2,4-oxadiazole-3-carboxamide has been provided. The new synthetic method provides great convenience for the synthesis of compounds containing 1,2,4-oxadiazole-3-carboxamide.

AB - 1,2,4-Oxadiazole-3-carboxamide has been extensively used in the pharmaceutical chemistry. In this study, 1,2,4-oxadiazole-3-carboxamide is accomplished through an acid-promoted reaction of N-(cyanomethyl)amide with nitrosation reagent. This novel preparation of 1,2,4-oxadiazole-3-carboxamide was carried out at 25 °C, and the yield of target compounds was as high as 92%. At the same time, the amount of acid used is reduced. A mechanism speculation for the formation of 1,2,4-oxadiazole-3-carboxamide has been provided. The new synthetic method provides great convenience for the synthesis of compounds containing 1,2,4-oxadiazole-3-carboxamide.

KW - 1,2,4-Oxadiazole-3-carboxamide

KW - Methyl 1,2,4-oxadiazole-3-carboxylate

KW - N-(Cyanomethyl)amide

KW - N′-Hydroxycarbamimidoyl cyanide

UR - https://www.scopus.com/pages/publications/85107681676

U2 - 10.1016/j.tetlet.2021.153209

DO - 10.1016/j.tetlet.2021.153209

M3 - 文章

AN - SCOPUS:85107681676

SN - 0040-4039

VL - 76

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153209

ER -

Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent: Facile synthesis of 1,2,4-oxadiazole-3-carboxamide

Abstract

Keywords

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