One-pot cascade synthesis of benzopyrans and dihydropyrano[c]chromenes catalyzed by lipase TLIM

Fu, Yajie; Lu, Zeping; Ma, Xiaolong; Fang, Ke; He, Xinyi; Xu, Huajin; Hu, Yi

doi:10.1016/j.bioorg.2020.103888

Cited by 16 publications

(8 citation statements)

References 30 publications

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“…Our data also showed that lipase TLIM had a broad spectrum of substrates, and the yield was still good after five repeated uses of the enzyme. 33 Compared with the traditional chemical methods, our reaction system offers great advantages in terms of temperature, catalyst reusability, and target product yield. [34][35][36] The reaction mechanism is proposed as following: first, the Knoevenagel condensation reaction of 4-chlorobenzaldehyde 1 and malononitrile 2 takes place to obtain intermediate product 4; then, 4 combined with 4-hydroxycoumarin 3 via the Michael addition reaction to obtain intermediate 5, which undergoes enolization, cyclization, and isomerization to produce the target product 6 (4H-pyran) (►Scheme 10).…”

Section: Synthesis Of Six-membered Heterocyclic Compounds Containing Oxygenmentioning

confidence: 99%

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 Six-membered Heterocyclic Compounds Containing Oxygenmentioning

confidence: 99%

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Wang

Shen

et al. 2021

Pharmaceutical Fronts

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“…1 H NMR (500 MHz, DMSO) δ 8.12 (d, J = 8.7 Hz, 2H), 7.99 (dd, J = 7.9, 1.4 Hz, 1H), 7.96 (s, 2H), 7.75 -7.70 (m, 1H), 7.52 (dd, J = 14.0, 8.2 Hz, 3H), 7.46 (d, J = 8.3 Hz, 1H), 4.82 (s, 1H), 3.99 (dd, J = 14.2, 5.9 Hz, 2H), 1.10 (t, J = 7.0 Hz, 3H). 13 [52] m.p. 208~210℃ ).…”

Section: Preparation Of Desmentioning

confidence: 99%

“…52 (m, 1H), 7.47 (dd, J = 8.0, 1.1 Hz, 1H), 7.39 -7.28 (m, 3H), 7.19 (td, J = 7.6, 1.1 Hz, 1H), 7.01 (td, J = 7.8, 1.7 Hz, 1H), 6.51 (s, 2H), 5.26 (s, 1H), 4.08 (dd, J = 7.1, 5.1 Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H).13 C NMR (126 MHz, CDCl3) δ 168.8, 160.3, 158.0, 153.5, 152.7, 142.1, 133.3, 132.8, 132.3, 128.2, 126.9, 124.2, 124.0, 122.3, 116.9, 113.2, 106.0, 79.1, 60.0, 36.4, 14.3. 4n: ethyl 2-amino-4-isopropyl-5-oxo-4H,5H-pyrano[3,2c]chromene-3-carboxylate Yellow liquid, yield: 25.0 mg (38%).…”

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confidence: 99%

One-Pot Synthesis of 4H-Pyrano[3,2-c]coumarin Derivatives Catalyzed by Deep Eutectic Solvent

Xie

Yang

et al. 2021

Synthesis

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4H-Pyrano[3,2-c]coumarin derivatives are an important class of pharmaceutical compounds that are expensive to prepare by previously reported methods. An efficient and green method was developed to obtain these derivatives using the deep eutectic solvent (DES) zinc chloride/acetamide (n:n = 1:4), which acted as both the catalyst and the solvent for the reaction. An aromatic aldehyde, 4-hydroxycoumarin, and cyanoacetate were used as the substrates. The DES, substrate molar ratio, diluent type, temperature, and reaction time were optimized to obtain the 4H-pyrano[3,2-c]coumarin derivatives from a range of aromatic aldehydes in a single step in moderate to high yields and under mild reaction conditions.

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“…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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One-pot cascade synthesis of benzopyrans and dihydropyrano[c]chromenes catalyzed by lipase TLIM

Cited by 16 publications

References 30 publications

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

One-Pot Synthesis of 4H-Pyrano[3,2-c]coumarin Derivatives Catalyzed by Deep Eutectic Solvent

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

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