Iodine promoted cyclization of <i>N</i>,<i>N</i>′-diphenylthiocarbamides with enaminones: a protocol for the synthesis of poly-substituted 2-iminothiazolines

Xu, Xiao-Hu; Dong, Zhi‐Bing

doi:10.1039/d2ob01477g

Cited by 4 publications

(1 citation statement)

References 39 publications

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“…On the basis of the literature, − a predicted reaction mechanism is proposed (Scheme ). Reactant 1a first reacts with a molecule of benzylamine in Cu(I) to form A , and another molecule of benzylamine reacts with iodine to form B .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1-Benzyl-2,4-diarylimidazole through I₂/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

Lv,

Chen,

et al. 2024

J. Org. Chem.

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In this paper, we report an innovative method for synthesizing 1-benzyl-2,4-diarylimidazole utilizing 1phenylethanone-2-(2-pyridinyl) hydrazine and benzylamine, catalyzed by an I 2 /CuI system. This approach represents a significant departure from traditional methods for synthesizing polysubstituted imidazoles; it employs the I 2 /CuI catalyst to replace rare metal catalysts, thereby achieving high yields of substitution products (≤85%). This method for the generation of 1,2,4-triimidazole derivatives is characterized by its exceptional chemical selectivity and extensive substrate compatibility.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1-Benzyl-2,4-diarylimidazole through I₂/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

Lv,

Chen,

et al. 2024

J. Org. Chem.

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I₂‐Promoted [3+2] Cyclization of Thiocarbamates with Enaminones: a Protocol for the Synthesis of Polysubstituted Thiazol‐2(3H)‐ones

Xu,

Weng,

Chen

et al. 2024

Adv Synth Catal

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An In‐Depth Review on Recent Progress in Synthetic Approaches and Biological Activities of Thiazol‐2(3H)‐Imine Derivatives

Saleem,

Shabir,

Rafique

et al. 2024

ChemistrySelect

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This review presents the in‐dept analysis of the synthetic approaches towards thiazol‐2(3H)‐imine and embarks at its various biological properties published during 2000 to 2023. The most important method of synthesis involves the reaction of substituted thioureas and α‐halo carbonyl compounds, and condensation and nucleophilic addition of 2‐amino‐1,3‐thiazoline with aldehydes. Additionally, isothiocyanate‐based multicomponent synthesis, and α‐nitroepoxides have been proved as benign precursors for this motif. Several eco‐friendly and solvent‐free synthesis from diazonium salts, acetylenes, tertiary enaminones and thiosemicarbazides have also been reported. This epitome is a unique combination of synthetic methods as well as biological activities like anti‐inflammatory, anti‐bacterial, anti‐cancer, anti‐leishmanial, anti‐microbial, herbicidal, anti‐HIV, and may be a valuable tool for researchers to tailor the synthetic procedures according to specific target structures and applications. Moreover, this review enlightens the applications of thiazol‐2(3H)‐imine as platelet GPIIB/IIIA receptor antagonists, alkaline phosphatase inhibitors, neurodegenerative drug Pifithrin‐α analogues, and skin whitening agents.

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Iodine promoted cyclization of N,N′-diphenylthiocarbamides with enaminones: a protocol for the synthesis of poly-substituted 2-iminothiazolines

Abstract: An iodine promoted cyclization reaction between N,N'-diphenylthiocarbamides and enaminones was achieved, providing a series of poly-substituted 2-iminothiazolines. The protocol features simple performance, transition metal free, broad functional group tolerance, good...

Cited by 4 publications

References 39 publications

Synthesis of 1-Benzyl-2,4-diarylimidazole through I₂/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

Synthesis of 1-Benzyl-2,4-diarylimidazole through I₂/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

I₂‐Promoted [3+2] Cyclization of Thiocarbamates with Enaminones: a Protocol for the Synthesis of Polysubstituted Thiazol‐2(3H)‐ones

An In‐Depth Review on Recent Progress in Synthetic Approaches and Biological Activities of Thiazol‐2(3H)‐Imine Derivatives

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Iodine promoted cyclization of N,N′-diphenylthiocarbamides with enaminones: a protocol for the synthesis of poly-substituted 2-iminothiazolines

Abstract: An iodine promoted cyclization reaction between N,N'-diphenylthiocarbamides and enaminones was achieved, providing a series of poly-substituted 2-iminothiazolines. The protocol features simple performance, transition metal free, broad functional group tolerance, good...

Cited by 4 publications

References 39 publications

Synthesis of 1-Benzyl-2,4-diarylimidazole through I2/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

Synthesis of 1-Benzyl-2,4-diarylimidazole through I2/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

I2‐Promoted [3+2] Cyclization of Thiocarbamates with Enaminones: a Protocol for the Synthesis of Polysubstituted Thiazol‐2(3H)‐ones

An In‐Depth Review on Recent Progress in Synthetic Approaches and Biological Activities of Thiazol‐2(3H)‐Imine Derivatives

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Product

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Synthesis of 1-Benzyl-2,4-diarylimidazole through I₂/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

Synthesis of 1-Benzyl-2,4-diarylimidazole through I₂/CuI-Catalyzed Cyclization of Benzylamine and Hydrazone

I₂‐Promoted [3+2] Cyclization of Thiocarbamates with Enaminones: a Protocol for the Synthesis of Polysubstituted Thiazol‐2(3H)‐ones