Biocatalytic One-Pot Three-Component Synthesis of Indoloquinolizines with High Diastereoselectivity

He, Wei-Xun; Xing, Xiu; Yang, Zeng‐Jie; Yuan, Yu; Wang, Na; Yu, Xiao‐Qi

doi:10.1007/s10562-019-02660-7

Cited by 13 publications

(4 citation statements)

References 43 publications

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“…Additionally, Yu et al. developed α‐amylase catalyse synthesis of highly substituted indoloquinolizines using tryptamines, β‐ketoesters and α, β‐unsaturated aldehydes . But, to the best of our knowledge there is no previous report of using α‐amylase as a catalyst for the aza‐Michael addition reaction of amines to enones.…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Aza‐Michael Addition of Aromatic Amines to Enone Using α‐Amylase in Water

et al. 2019

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The Michael addition of amines with enones for synthesizing β‐amino carbonyls constitutes a valuable transformation in organic chemistry. While various catalyst have been made available for catalyzing the Michael addition of aromatic amines to enones but there is no report of using α‐amylase enzyme to catalyze this transformation. The α‐amylase from Aspergillus oryzae was found to catalyze the Michael addition of various aryl (hetero) amines to methyl vinyl ketone with high catalytic efficiency (63–83% yield). A hybrid of α‐amylase with copper nanoparticle (α‐amylase@CuNPs) has been prepared and used to catalyze this transformation as a reusable catalyst. Further, an application of α‐amylase catalyzed aza‐Michael addition in the cascade reactions has been exhibited by synthesizing biologically important 3‐acetyl quinoline. In addition, molecular docking and molecular dynamics (MD) simulation studies are carried out to get insight into the key interactions of the substrates with the amino acid residues near the active site and the probable reaction mechanism, which reveals Glu230 and Asn295 play a crucial role in the substrate activation process.

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Section: Introductionmentioning

confidence: 99%

Biocatalytic Aza‐Michael Addition of Aromatic Amines to Enone Using α‐Amylase in Water

et al. 2019

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“…For example, α-amylase activation catalysis is an alternative protocol for the generation of highly substituted indoquinolines 113 , which was uncovered by He and coworkers in 2019 ( Scheme 27 ). 93 The reaction using tryptamines 110, β-keto esters 111 , and α,β-unsaturated aldehydes 112 as starting materials afforded a variety of products in moderate to good yields.…”

Section: Three-component Pictet–spengler Cyclization-based Domino Rea...mentioning

confidence: 99%

Pictet–Spengler-Based Multicomponent Domino Reactions to Construct Polyheterocycles

Hu,

Huang,

Feng

2023

Pharmaceutical Fronts

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The Pictet–Spengler reaction is one of the important methodological arsenals in synthetic and medicinal chemistry, acting as an amenable tool for preparing tetrahydroisoquinoline, tetrahydro-β-carbolines, polycyclic skeletons, and value-added products. More than 100 years after its initial discovery, the Pictet–Spengler reaction's response has not withdrawn from the stage, but it has once again become the focus of attention with new features. The review summarizes recent advances in Pictet–Spengler-based multicomponent reactions from 2007 to 2022, including three-component and four-component Pictet–Spengler cyclization reactions in the presence of metal catalysts, organocatalysts, biological enzyme catalysts, and so on. These Pictet–Spengler-based multicomponent protocols provide an atom-/step economic approach for the synthesis of a library of new chemical entities.

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“…[32] Furthermore, a reaction between tryptamines, βketoesters and α,β-unsaturated aldehydes using α-amylase as a catalyst for the formation of highly substituted indoloquinolizines was established by Yu et al. [33] Recently, we have reported the Michael addition reaction of aromatic amines with methyl vinyl ketone in the presence of the α-amylase enzyme. [34] Keeping in view the medicinal application of BIMs and our previous experience in biocatalysis, herein, we hypothesized to use α-amylase enzyme as a biocatalyst for the synthesis of bis(indolyl)methanes.…”

Section: Introductionmentioning

confidence: 98%

“…Furthermore, a reaction between tryptamines, β‐ketoesters and α,β‐unsaturated aldehydes using α‐amylase as a catalyst for the formation of highly substituted indoloquinolizines was established by Yu et al. [33] . Recently, we have reported the Michael addition reaction of aromatic amines with methyl vinyl ketone in the presence of the α‐amylase enzyme [34] .…”

Section: Introductionmentioning

confidence: 99%

Construction of Bis‐Indole Derivatives Using α‐Amylase Enzyme: Application in the Gram‐Scale Synthesis of Bis‐Indole Containing Bioactive Molecules

Kamboj

Tyagi

2023

Asian J Org Chem

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Herein, we have developed a biocatalytic approach toward the synthesis of bis(indolyl)methane using an α‐amylase in water. This protocol has a number of advantages like eco‐friendly reaction conditions, use of biodegradable catalyst, and higher conversion. Moreover, the generality of this protocol was displayed by employing various substitutions on indole and benzaldehyde which provides the corresponding products in very good yield (63–89%). Also, the applicability of this protocol was shown by synthesizing four different bioactive molecules on a gram scale.

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Biocatalytic One-Pot Three-Component Synthesis of Indoloquinolizines with High Diastereoselectivity

Cited by 13 publications

References 43 publications

Biocatalytic Aza‐Michael Addition of Aromatic Amines to Enone Using α‐Amylase in Water

Biocatalytic Aza‐Michael Addition of Aromatic Amines to Enone Using α‐Amylase in Water

Pictet–Spengler-Based Multicomponent Domino Reactions to Construct Polyheterocycles

Construction of Bis‐Indole Derivatives Using α‐Amylase Enzyme: Application in the Gram‐Scale Synthesis of Bis‐Indole Containing Bioactive Molecules

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