Microwave-assisted controllable synthesis of 2-acylbenzothiazoles and bibenzo[b][1,4]thiazines from aryl methyl ketones and disulfanediyldianilines

Qi, Yuquan; Gu, Xiaoyu; Huang, Xianqiang; Shen, Guodong; Yang, Bingchuan; He, Qingpeng; Xue, Zheng; Du, Mengcheng; Shi, Lilong; Yu, Bing

doi:10.1016/j.cclet.2021.05.069

Cited by 22 publications

(27 citation statements)

References 36 publications

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“…N -Heteroaromatics scaffolds are common in pharmaceuticals and natural products. 15 For instance, the selected examples of biologically active molecules in Fig. 1 contain the scaffold of azauracil, quinoxalin-2(1 H )-one, and 2 H -benzo[ b ][1,4]oxazin-2-one.…”

Section: Introductionmentioning

confidence: 99%

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics

Cheng,

Fan,

et al. 2023

Green Chem.

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Section: Introductionmentioning

confidence: 99%

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics

Cheng,

Fan,

et al. 2023

Green Chem.

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“…Established on the obtained results and literature evidences, [57,58] More recently, Yu and co-workers have described the Microwave assisted synthesis of 2-acylbenzothiazoles 114 and bibenzo[b][1,4]thiazines from disulfanediyldianilines 112 and aryl methyl ketones 113 using I 2 /DMSO or I 2 /MeCN reagent systems, respectively (Scheme 51). [73] The reaction was switchable by simply changing the reaction conditions (I 2 /MeCN or I 2 / DMSO) without the involvement of hazardous oxidants and additional activating reagents.…”

Section: Eyad a Younes Earned His Phd Degree At Memorial University O...mentioning

confidence: 99%

Strategies towards the Synthesis of 2‐Ketoaryl Azole Derivatives using C‐H Functionalization Approach and 1,2‐Bis‐Nucleophile Precursors

et al. 2023

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A spectrum of compounds attached to 2‐keto aryl azole moieties are found as pivotal building blocks in medicinal chemistry and drug discovery. This is why, the collection of novel methods have been described for the synthesis of these compounds, which are of great significance among organic chemists interested towards the development of new synthetic methods in the fields of natural products, bioactive molecules and materials sciences. This review presents the important breakthrough achieved during last decade towards improvement of approaches for the synthesis of these molecules.

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“…Benzoselenazoles have not been explored much compared to benzoxazoles and benzothiazoles . Moreover, diverse synthetic approaches have been employed for the construction of 1,3-benzoselenazoles (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Reactions, and Antioxidant Properties of Bis(3-amino-1-hydroxybenzyl)diselenide

et al. 2023

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Bis(3-amino-1-hydroxybenzyl)diselenide containing two ortho groups was synthesized from 7-nitro-3H-2,1-benzoxaselenole and in situ generated sodium benzene tellurolate (PhTeNa). One-pot synthesis of 1,3-benzoselenazoles was achieved from bis(3-amino-1-hydroxybenzyl)diselenide and aryl aldehydes using acetic acid as a catalyst. The X-ray crystal structure of chloro-substituted benzoselenazole revealed a planar structure with T-shaped geometry around the Se atom. Both natural bond orbital and atoms in molecules calculations confirmed the presence of secondary Se···H interactions in bis(3-amino-1-hydroxybenzyl)diselenide and Se···O interactions in benzoselenazoles, respectively. The glutathione peroxidase (GPx)-like antioxidant activities of all compounds were evaluated using a thiophenol assay. Bis(3-amino-1-hydroxybenzyl)diselenide and benzoselenazoles showed better GPx-like activity compared to that of the diphenyl diselenide and ebselen, used as references, respectively. Based on 77Se{1H} NMR spectroscopy, a catalytic cycle for bis(3-amino-1-hydroxybenzyl)diselenide using thiophenol and hydrogen peroxide was proposed involving selenol, selenosulfide, and selenenic acid as intermediates. The potency of all GPx mimics was confirmed by their in vitro antibacterial properties against the biofilm formation of Bacillus subtilis and Pseudomonas aeruginosa. Additionally, molecular docking studies were used to evaluate the in silico interactions between the active sites of the TsaA and LasR-based proteins found in Bacillus subtilis and Pseudomonas aeruginosa.

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Microwave-assisted controllable synthesis of 2-acylbenzothiazoles and bibenzo[b][1,4]thiazines from aryl methyl ketones and disulfanediyldianilines

Cited by 22 publications

References 36 publications

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics

Strategies towards the Synthesis of 2‐Ketoaryl Azole Derivatives using C‐H Functionalization Approach and 1,2‐Bis‐Nucleophile Precursors

Synthesis, Reactions, and Antioxidant Properties of Bis(3-amino-1-hydroxybenzyl)diselenide

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