Recent advances in the synthesis and utility of thiazoline and its derivatives

Kumar, Sumit; Arora, Aditi; Sapra, Shivani; Kumar, Rajesh; Singh, Brajendra K.; Singh, Sunil K.

doi:10.1039/d3ra06444a

RSC Adv.

2024

DOI: 10.1039/d3ra06444a

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Recent advances in the synthesis and utility of thiazoline and its derivatives

Sumit Kumar,

Aditi Arora,

Shivani Sapra

et al.

Abstract: Thiazolines and their derivatives hold significant importance in the field of medicinal chemistry due to their promising potential as pharmaceutical agents.

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Cited by 8 publications

References 166 publications

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Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

Zhang,

Chen,

Liu

et al. 2024

Asian J Org Chem

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We developed a novel method for the synthesis of 2‐substituted‐4,5‐dihydrothiazol‐4‐ols compounds through cyclization of thioamides and 1,4‐dithiane‐2,5‐diol in the presence of Et3N. Stable hydroxy‐substituted thiazole compounds were isolated of substituted thioamides. The reaction conditions are simple, the substrate range is wide, and the target compounds were obtained in up to 82% yield.

show abstract

Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

Zhang,

Chen,

Liu

et al. 2024

Asian J Org Chem

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Chemoenzymatic Synthesis of 2‐Aryl Thiazolines from 4‐Hydroxybenzaldehydes Using Vanillyl Alcohol Oxidases

Zhang,

Xie,

Yang

et al. 2024

Angewandte Chemie

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Nitrogen heterocycles are commonly found in bioactive natural products and drugs. However, the biocatalytic tools for nitrogen heterocycle synthesis are limited. Herein, we report the discovery of vanillyl alcohol oxidases (VAOs) as efficient biocatalysts for the one‐pot synthesis of 2‐aryl thiazolines from various 4‐hydroxybenzaldehydes and aminothiols. The wild‐type biocatalyst features a broad scope of 4‐hydroxybenzaldehydes. Though the scope of aminothiols is limited, it could be improved via semi‐rational protein engineering, generating a variant to produce previously inaccessible cysteine‐derived bioactive 2‐aryl thiazolines using the wild‐type VAO. Benefiting from the derivatizable functional groups in the enzymatic products, we further chemically modified these products to expand the chemical space, offering a new chemoenzymatic strategy for the green and efficient synthesis of structurally diverse 2‐aryl‐thiazoline derivatives to prompt their use in drug discovery and catalysis.

show abstract

Chemoenzymatic Synthesis of 2‐Aryl Thiazolines from 4‐Hydroxybenzaldehydes Using Vanillyl Alcohol Oxidases

Zhang,

Xie,

Yang

et al. 2024

Angew Chem Int Ed

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Recent advances in the synthesis and utility of thiazoline and its derivatives

Abstract: Thiazolines and their derivatives hold significant importance in the field of medicinal chemistry due to their promising potential as pharmaceutical agents.

Cited by 8 publications

References 166 publications

Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

Chemoenzymatic Synthesis of 2‐Aryl Thiazolines from 4‐Hydroxybenzaldehydes Using Vanillyl Alcohol Oxidases

Chemoenzymatic Synthesis of 2‐Aryl Thiazolines from 4‐Hydroxybenzaldehydes Using Vanillyl Alcohol Oxidases

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