Efficient synthesis of cyano-containing multi-substituted indoles catalyzed by lipase

Li, Fengxi; Xu, Yaning; Wang, Ciduo; Wang, Chunyu; Zhao, Ruihong

doi:10.1016/j.bioorg.2020.104583

Cited by 17 publications

(9 citation statements)

References 34 publications

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“…In 2021, Li et al first reported Candida rugosa lipase (CRL)-catalyzed reaction of 1,3-diketones with fumaronitrile to synthesize polycyanosubstituted indole with moderate to excellent yields (►Scheme 2A). 15 This report also suggested that steric hindrance of R 1 and R 2 decreased the total yield of the target product. Encouragingly, when the substrate is an asymmetric 1,3-diketone, a higher regioselectivity and total yield of the reaction were achieved when compared with a chemical catalysis method.…”

Section: Synthesis Of Five-membered Heterocyclic Compounds Containing Nitrogenmentioning

confidence: 83%

“…Lipase can be used to catalyze intramolecular transesterification of hemithioacetals to synthesize 1,3-oxathiolan-5one derivatives (►Scheme 15) with the best reactivity being found in lipase CALB or novozyme 435. 46 The reaction mechanism may be attributed to the following: first, under the catalysis of triethylamine, 1 (2-methylpropanal) and 2 (octanal) [or, 3 (pyridine-2-carbaldehyde)] react with mercaptan A (methyl 2-mercaptoacetate) or mercaptan B (methyl-3-mercaptopropionate) to produce γ-and d-hydroxyl ester intermediates 1A-3A and 1B-3B, respectively.…”

Section: Synthesis Of Other Heterocyclic Compoundsmentioning

confidence: 99%

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Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Wang

Shen

et al. 2021

Pharmaceutical Fronts

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Heterocyclic compounds are representative of a larger class of organic compounds, and worthy of attention for many reasons, chief of which is the participation of heterocyclic scaffolds in the skeleton structure of many drugs. Lipases are enzymes with catalytic versatility, and play a key role in catalyzing the reaction of carbon–carbon bond formation, allowing the production of different compounds. This article reviewed the lipase-catalyzed aldol reaction, Knoevenagel reaction, Michael reaction, Mannich reaction, etc., in the synthesis of several classes of heterocyclic compounds with important physiological and pharmacological activities, and also prospected the research focus in lipase-catalyzed chemistry transformations in the future.

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Section: Synthesis Of Five-membered Heterocyclic Compounds Containing Nitrogenmentioning

confidence: 83%

Section: Synthesis Of Other Heterocyclic Compoundsmentioning

confidence: 99%

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Wang

Shen

et al. 2021

Pharmaceutical Fronts

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“…[39] Based on our experimental results and previous studies, a reasonable mechanism for this MCR is proposed in Scheme 3. [40][41][42] First, aldehydes (2) and sulfonamides (3) form 5 via spontaneous nucleophilic addition. Dehydration then generates sulfonamides via reversible reactions.…”

Section: Chemistryselectmentioning

confidence: 99%

Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Wang

et al. 2022

ChemistrySelect

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In this study, supercritical carbon dioxide (ScCO2), which is a sustainable and green solvent, was used as a reaction medium in the lipase‐catalyzed synthesis of anthrone‐functionalized benzylic amines for the first time. We synthesized the target compounds via a lipase‐catalyzed multicomponent cascade reaction of aldehydes, sulfonamides, and anthrones in ScCO2. The reaction can be accomplished in good‐to‐excellent yields (77 %–95 %) and can exhibit good functional group tolerance. In brief, the reaction was characterized by step economy, metal‐free conditions, environmentally friendly solvents, and biocatalysts.

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“…[22][23][24][25][26] In this area, lipases demonstrate the outstanding catalytic promiscuous abilities for their excellent stability and broad specificity, and many elegant works have been reported. [27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] As a further study to develop new types of organic reactions catalyzed by lipase, we reported here an efficient and mild method for the synthesis of N′-alkyl benzohydrazides (Scheme 1). To our knowledge, this is the first instance using enzyme as catalyst for a hydrazine insertion to synthesize benzohydrazides.…”

Section: S C H E M E 1 Synthesis Of N′-alkyl Benzohydrazides Catalyze...mentioning

confidence: 99%

“…Recently, enzyme catalytic promiscuity, the ability of a single active site of enzyme to catalyze new types of reactions that are different from natural ones, has been developed to widen the application of enzyme in organic synthesis 22–26 . In this area, lipases demonstrate the outstanding catalytic promiscuous abilities for their excellent stability and broad specificity, and many elegant works have been reported 27–45 . As a further study to develop new types of organic reactions catalyzed by lipase, we reported here an efficient and mild method for the synthesis of N′‑alkyl benzohydrazides (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Lipase‐catalyzed hydrazine insertion for the synthesis of N′‐alkyl benzohydrazides

et al. 2022

Biotech and App Biochem

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N′-alkyl benzohydrazides are classic organic compounds that have been widely utilized in organic chemistry. In this study, an efficient method was developed for the synthesis of N′-alkyl benzohydrazides by hydrazine insertion catalyzed by lipase. Under the optimal conditions (Morita-Baylis-Hillman ketone [1 mmol], phenylhydrazine [1.3 mmol], N,N-dimethylformamide [2 ml], lipase [20 mg], room temperature, 12 h), satisfactory yields (71-97%) and substrate tolerance were obtained when porcine pancreatic lipase was used as biocatalyst. These findings imply the great potential for the lipase-catalyzed synthesis of N′-alkyl benzohydrazides and extend the utilization of lipase in organic chemistry.

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Efficient synthesis of cyano-containing multi-substituted indoles catalyzed by lipase

Cited by 17 publications

References 34 publications

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Lipase‐catalyzed hydrazine insertion for the synthesis of N′‐alkyl benzohydrazides

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