Research Progress for the Thiolysis Reaction of Halobenzonitrile

Li, Shanshan; Hong, Hailong; Han, Limin; Zhang, Tianmiao; Wang, Yunlong; Zhu, Ning

doi:10.6023/cjoc201707002

Chin. J. Org. Chem.

2018

DOI: 10.6023/cjoc201707002

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Research Progress for the Thiolysis Reaction of Halobenzonitrile

Shanshan Li¹,

Hailong Hong²,

Limin Han³

et al.

Abstract: Halobenzonitrile is an important raw material in the fields of medicine, pesticide and materials. Halobenzonitrile has a nitrile group and a halo group which all could react with nucleophile reagents. The law for the selective synthesis of halothiobenzamide or mercaptobenzonitrile from the reaction of halobenzonitrile and different sulfur source is summarized. It is found that the halothiobenzamide product could be synthesized under protonic acid condition from halobenzonitrile, while the mercaptobenzonitrile … Show more

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Cited by 4 publications

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Selectively Oxidative Thiolysis of Nitriles into Primary Thioamides and Insecticidal Application

Huang

Guo

et al. 2020

Asian J Org Chem

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Primary thioamides are useful building blocks for drug and insecticide development, therefore an environmentally benign synthesis of primary thioamides is desired. This paper discloses an oxidative thiolysis for the selective transformation of nitriles into primary thioamides using elemental sulfur or thiuram in the presence of K2S2O8 in DMF/H2O. This practical method enables access to a wide range of synthetically and pharmaceutically useful primary thioamides. Advantages of this reaction include transition‐metal‐free and base‐free reaction conditions, use of an environmentally benign solvent (DMF/H2O) system, the use of non‐toxic elemental sulfur or thiuram as the sulfur sources, and good functional groups tolerances with excellent selectivity. Furthermore, the insecticide Fipronil can also be converted to the corresponding thioamide and maintains excellent bioactivity against P. xylostella. The LC50 value of Fipronil thioamide is 1.25 mg/L.

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Selectively Oxidative Thiolysis of Nitriles into Primary Thioamides and Insecticidal Application

Huang

Guo

et al. 2020

Asian J Org Chem

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Direct synthesis of 2-substituted benzonitriles via alkylcyanation of arynes with N,N-disubstituted aminomalononitriles

et al. 2020

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A Domino One-Pot Approach to Functionalized Benzonitriles from 2-[(3-Hydroxy/acetoxy)propyn-1-yl]benzamides

Nair,

Chinta,

Baire

2024

Synthesis

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Functionalized benzonitriles, α,β-epoxyketones and β-hydroxy-α-haloketones are part of several medicinally important molecules. The benzonitriles possessing any of these functional groups may be of interest to medicinal chemists for further study. However, simultaneous incorporation of the nitrile group and these functional groups into the aromatic ring is a challenging task. Herein we report such an important strategy for the rapid and simultaneous construction of structurally novel benzonitrile derivatives, possessing either an ortho--iodo--hydroxyketones or an -epoxyketones or an -enone, from an unprotected, 2-[(3-hydroxy/acetoxy)-propyn-1-yl]benzamides. These benzonitriles are unique in their structural features and have been reported for the first time. This process involves NXS promoted dehydration¬–halohydration followed by DIPEA promoted either an epoxide formation (for alcohols). We have developed both stepwise as well as one-pot strategies to improve synthetic efficiency. No metal catalysts are employed in this process. These methods show good substrate scope and yields.

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Research Progress for the Thiolysis Reaction of Halobenzonitrile

Cited by 4 publications

References 13 publications

Selectively Oxidative Thiolysis of Nitriles into Primary Thioamides and Insecticidal Application

Selectively Oxidative Thiolysis of Nitriles into Primary Thioamides and Insecticidal Application

Direct synthesis of 2-substituted benzonitriles via alkylcyanation of arynes with N,N-disubstituted aminomalononitriles

A Domino One-Pot Approach to Functionalized Benzonitriles from 2-[(3-Hydroxy/acetoxy)propyn-1-yl]benzamides

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