One-pot protocol for the reductive amination of aldehydes using thiamine hydrochloride as a green catalyst under solvent-free condition

Patil, Shripad M.; Bedre, Ashwini; Gade, Vilas B.; Jopale, Manohar K.; Bhagat, Ravindra S.; Pise, Ashok S.

doi:10.1080/00397911.2023.2236258

Cited by 10 publications

(2 citation statements)

References 70 publications

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“…[31] Another report was made on thiamine hydrochloride catalysed reaction between aldehyde and amines in presence of sodium borohydrate. [32] Similarly, ZnCl2, I2 and KI were reported as a catalyst in various reports on synthesizing new heterocycles. [33][34][35][36] In present work, we have synthesized bisindoles containing pyridine and pyrimidine derivatives incorporating green synthesis using thiamine hydrochloride as catalyst and water as solvent.…”

Section: Introductionmentioning

confidence: 99%

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

Poonacha,

Metri,

et al. 2024

ChemistrySelect

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Indoles and their derivatives have long been studied for their anticancer properties. Breast cancer has been treated using indole‐3‐carbinol, Indirubins, and many other naturally occurring indoles as well as their synthesized equivalents. It has been determined that the AKT pathway is a prospective target for therapeutic strategies in the treatment of breast cancer. The dysregulation of AKT pathway frequently promotes cell proliferation, survival, and resistance to apoptosis. We synthesized a novel group of bisindole clubbed pyridine and pyrimidine derivatives 5(a–l) using water as the solvent and thiamine hydrochloride as the catalyst. Compounds 5 a, 5 c, 5 d, 5 e, and 5 f are the most active against MCF‐7 cells, with an IC50 values of 2.48±0.39, 1.35±0.13, 3.36±0.53, 4.05±0.61 and 1.91±0.28 μM, respectively. Further, in silico docking of the active compound 5 c had the highest binding energy of −10.59 kcal/mol. Additionally, molecular dynanamics simulations were performed for better understanding the mode of interaction of ligand and protein. In conclusion, we have synthesized bisindoles using thiamine hydrochloride as a catalyst that target AKT pathway in breast cancer cells.

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Section: Introductionmentioning

confidence: 99%

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

Poonacha,

Metri,

et al. 2024

ChemistrySelect

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“…There are many methods for the synthesis of amines, such as the amination of halogenated hydrocarbons, the hydrogenation of nitrile compounds, the amination of olefins, the reduction of nitroaromatic compounds [15,16], and the reductive amination of aldehydes/ketones/alcohols [17][18][19][20][21][22][23]. With the continuous improvement of the petroleum industry and the production of biomass-based alcohol compounds, the reductive amination of alcohols is becoming the most promising and effective method because of its abundant source materials, low cost, and simple process [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

The Acquisition of Primary Amines from Alcohols through Reductive Amination over Heterogeneous Catalysts

Huang,

Wei,

Cheng

et al. 2023

Catalysts

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The synthesis of primary amines via the reductive amination of alcohols involves a hydrogen-borrowing or hydrogen-transfer mechanism, which consists of three main steps: alcohol hydroxyl dehydrogenation, carbonyl imidization, and imine hydrogenation. Heterogeneous catalysts are widely used for this reaction because of their high performance and amenability to separation and reuse. However, the efficiency of reductive amination is limited by the dehydrogenation step, which is severely affected by the competitive adsorption of NH3. We hope to improve the efficiency of reductive amination by increasing dehydrogenation efficiency. Therefore, in this overview, we introduce the research progress of alcohol reductive amination reaction catalyzed by heterogeneous metal catalysts, focusing on methods of enhancing dehydrogenation efficiency by screening the metal component and the acidity/alkalinity of the support. Finally, we propose some new strategies for the preparation of catalysts from the perspective of overcoming the competitive adsorption of NH3 and speculate on the design and synthesis of novel catalysts with high performance in the future.

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Thiamine (Vitamin B1) Promoted Organic Transformations: A Recent Updates

Shaw,

Prakash

2024

Chemistry An Asian Journal

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Due to the growing significance of sustainable and environmentally friendly organic transformations, there has been increasing interest in utilizing vitamins as catalysts owing to their green nature, biocompatibility, and ease of preparation. Among these, Vitamin B1, also known as thiamine stands out for its nonflammable, water‐soluble, inexpensive, and non‐toxic characteristics. This review summarized recent developments on the catalytic application of Vitamin B1 in organic transformations, particularly in facilitating C‐C and C‐X (N, O, S) bond formations, thus demonstrating its efficacy in synthesizing complex molecules. Vitamin B1 exhibits versatility in these reactions, functioning as both an organocatalyst as well as a co‐catalyst or ligand with other metal catalysts. The review also delves into the application of thiamine diphosphate ‐dependent enzymes as catalysts in organic reactions, drawing inspiration from natural enzymatic processes. Additionally, the mechanistic intricacies of thiamine‐catalyzed reactions and the roles of co‐catalysts or additives are thoroughly examined, providing insights into reaction pathways and facilitating informed catalyst design strategies.

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One-pot protocol for the reductive amination of aldehydes using thiamine hydrochloride as a green catalyst under solvent-free condition

Cited by 10 publications

References 70 publications

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

Development of Novel Pyridine and Pyrimidine Clubbed Bisindoles as Inhibitors of AKT Pathway

The Acquisition of Primary Amines from Alcohols through Reductive Amination over Heterogeneous Catalysts

Thiamine (Vitamin B1) Promoted Organic Transformations: A Recent Updates

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