Co(III)-Catalyzed Stereospecific Synthesis of (E)-Homoallylic Alcohols with 4-vinyl-1,3-dioxan-2-ones: Late-Stage C−H Homoallylation of indole derivatives

2021 ◽  
Author(s):  
Hong Hu ◽  
Wenhua Xu ◽  
Wu-Xiang Kang ◽  
Wei Sun ◽  
Rui Sun ◽  
...  
Keyword(s):  
Late Stage ◽  
High Efficiency ◽  
Stereospecific Synthesis ◽  
Indole Derivatives ◽  
Reaction Conditions ◽  
Homoallylic Alcohols

An unprecedented Co(III)-catalyzed stereoselective C−H homoallylation reaction of indole derivatives with 4-vinyl-1,3-dioxan-2-ones to access (E)-homoallylic alcohols has been developed. This protocol exhibits mild reaction conditions, high efficiency, good yields, excellent...

Palladium-Catalyzed Cross-Coupling Reactions of 4-Tosyl­oxyquinazolines with Indoles: An Efficient Approach to 4-(1H-Indol-1-yl)quinazolines

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 383-390 ◽  
Author(s):  
Yiyuan Peng ◽  
Xinglin Ye ◽  
Jian Huang ◽  
Zhihong Deng ◽  
Jianjun Yuan
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Indole Derivatives ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

In this paper, exploration of our continuous interests on late-stage derivation of quinozaline core is described. A wide array of 4-(1H-indol-1-yl)quinazolines were obtained in good to excellent yields through palladium-catalyzed cross-coupling of 4-tosyloxyquinazolines with indole derivatives under mild reaction conditions.

scholarly journals Kinetic resolution of indolines by asymmetric hydroxylamine formation

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Gang Wang ◽  
Ran Lu ◽  
Chuangchuang He ◽  
Lei Liu
Keyword(s):  
Hydrogen Peroxide ◽  
Chemical Synthesis ◽  
Late Stage ◽  
Kinetic Resolution ◽  
High Efficiency ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Environmentally Benign ◽  
Secondary Amines

AbstractCatalytic kinetic resolution of amines represents a longstanding challenge in chemical synthesis. Here, we described a kinetic resolution of secondary amines through oxygenation to produce enantiopure hydroxylamines involving N–O bond formation. The economic and practical titanium-catalyzed asymmetric oxygenation with environmentally benign hydrogen peroxide as oxidant is applicable to a range of racemic indolines with multiple stereocenters and diverse substituent patterns in high efficiency with efficient chemoselectivity and enantio-discrimination. Late-stage asymmetric oxygenation of bioactive molecules that are otherwise difficult to synthesize was also explored.

Late-Stage Sulfoximination: Improved Synthesis of the Anticancer Drug Candidate Atuveciclib

Synthesis ◽  
2018 ◽  
Vol 51 (04) ◽  
pp. 971-975 ◽  
Author(s):  
Vincent Reboul ◽  
Thomas Glachet ◽  
Xavier Franck
Keyword(s):  
Anticancer Drug ◽  
Late Stage ◽  
Drug Candidate ◽  
Efficient Synthesis ◽  
Reaction Conditions

An efficient synthesis of racemic atuveciclib was accomplished in five steps with an excellent 51% overall yield, using cheap reagents and mild reaction conditions. The key sulfoximination reaction was realized during the last step of the synthesis from the corresponding sulfide.

scholarly journals Application of enzyme engineering in pharmacy

2020 ◽  
Vol 9 (2) ◽  
Author(s):  
Qiaole Li ◽  
Yanhong Li ◽  
Haoran Niu
Keyword(s):  
High Efficiency ◽  
Development Trend ◽  
Enzyme Engineering ◽  
Reaction Conditions ◽  
Important Method ◽  
Reaction Specificity ◽  
Prevention And Treatment ◽  
Modern Biotechnology ◽  
Catalytic Functions ◽  
The Development Trend

Enzyme engineering is an important part of modern biotechnology. Due to its high reaction specificity, high efficiency, mild reaction conditions, and low pollution, it is also an important method widely used in the pharmaceutical field. The application of enzymes in medicine is diverse, such as: diagnosis, prevention and treatment of diseases with enzymes, manufacture of various drugs with enzymes, etc., mainly through manual operations, to obtain enzymes required by the pharmaceutical industry, and through various means Enzymes perform their catalytic functions. This article mainly introduces the application of enzyme engineering in the pharmaceutical field, and also prospects the development trend of enzyme engineering in the pharmaceutical field.

A mild heteroatom (O-, N-, and S-) methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2 combination

Synthesis ◽  
2022 ◽  
Author(s):  
Yu Tang ◽  
Biao Yu
Keyword(s):  
Cost Efficiency ◽  
Room Temperature ◽  
High Efficiency ◽  
Attractive Alternative ◽  
Indole Derivatives ◽  
Trimethyl Phosphate ◽  
Environmental Friendly ◽  
Operational Simplicity

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2 combination has been developed, which proceeds in DMF, or water, or under neat conditions at 80 oC or at room temperature. A series of O-, N- and S-nucleophiles, including phenols, sulfonamides, N-heterocycles such as 9H-carbazole, indole derivatives, 1,8-naphthalimide, and aryl/alkyl thiols are suitable substrates of this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmental friendly nature of this protocol make it an attractive alternative to the conventional base prompted heteroatom methylation procedures.

Peroxovanadates and Its Bio-Mimicking Relation with Vanadium Haloperoxidases

2016 ◽  
pp. 197-219
Author(s):  
Pranjal Saikia ◽  
Saitanya Kumar Bharadwaj ◽  
Abu Taleb Miah
Keyword(s):  
Amino Acids ◽  
Active Site ◽  
High Efficiency ◽  
Recombinant Enzymes ◽  
Vanadium Compounds ◽  
Reaction Conditions ◽  
The Cost ◽  
Major Emphasis ◽  
Protein Active Site

Vanadium Haloperoxidases (VHPOs) have been used in a variety of biotransformations showing remarkable stereoselectivity and regiospecificity. The high efficiency of the enzyme is influenced by the protein active site and the role of certain amino acids in activation of vanadium(V)-bound peroxide for halide oxidation. The use of natural or recombinant enzymes, or biomimetic vanadium compounds brings up issues regarding the cost of production and reaction conditions. In this chapter, the primary intent is to provide a simple and clear picture of functional mimicking nature of peroxovanadium compounds with haloperoxidases enzymes to the readers. Major emphasis would be given to examine the reactivity of the vanadium haloperoxidases with mechanism.

Photocatalytic Intramolecular [2 + 2] Cycloaddition of Indole Derivatives via Energy Transfer: A Method for Late-Stage Skeletal Transformation

ACS Catalysis ◽  
2020 ◽  
Vol 10 (17) ◽  
pp. 10149-10156 ◽  
Author(s):  
Zhijie Zhang ◽  
Dong Yi ◽  
Min Zhang ◽  
Jun Wei ◽  
Ji Lu ◽  
...  
Keyword(s):  
Energy Transfer ◽  
Late Stage ◽  
Indole Derivatives ◽  
Skeletal Transformation

scholarly journals Microwave-Assisted Heating Reactions of N-Acetylglucosamine (GlcNAc) in Sulfolane as a Method Generating 1,6-Anhydrosugars Consisting of Amino Monosaccharide Backbones

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1944
Author(s):  
Harumi Kaga ◽  
Masaru Enomoto ◽  
Hiroki Shimizu ◽  
Izuru Nagashima ◽  
Keigo Matsuda ◽  
...  
Keyword(s):  
Optimal Condition ◽  
General Feature ◽  
Time Course ◽  
High Efficiency ◽  
Raw Materials ◽  
Reaction Conditions ◽  
Microwave Assisted ◽  
High Potentials ◽  
Course Changes

The microwave-assisted heating reaction of N-acetyl glucosamine (GlcNAc) in sulfolane is described. The reaction produces two major products that are assignable to 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucopyranose (AGPNAc) and 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucofuranose (AGFNAc). In order to reveal a general feature of the system, the 3, 5, and 10 min reactions were performed at 140, 160, 180, 200, and 220 °C to clarify the time course changes in the conversion of GlcNAc and the yields of the two produced 1,6-anhydrosugars. Temperature is a crucial factor that significantly affects the conversion of GlcNAc. The yields of AGPNAc and AGFNAc are also drastically changed depending on the reaction conditions. The 5-min reaction at 200 °C is shown to be the optimal condition to generate the 1,6-anhydrosugars with a high efficiency in which AGPNAc and AGFNAc are produced in the yields of 21% and 44%, respectively. Consequently, the microwave-assisted heating reaction of GlcNAc in sulfolane is shown to be a simple and promising pathway to generate 1,6-anhydrosugars consisting of amino monosaccharide backbones, which have high potentials as raw materials leading to biological oligosaccharides and biomimetic polysaccharides.

scholarly journals Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Zhan Li ◽  
Ke-Feng Wang ◽  
Xin Zhao ◽  
Huihui Ti ◽  
Xu-Ge Liu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Late Stage ◽  
Materials Science ◽  
Reaction Pathway ◽  
Chemical Conversion ◽  
Primary Amines ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Aliphatic Acids ◽  
Redox Active

Abstract Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.

Ionic liquid promoted and mediated green preparation of arylbispyranylmethane and pyran derivatives and their hybrid with a pyrimidine nucleoside

2009 ◽  
Vol 2009 (8) ◽  
pp. 473-477 ◽  
Author(s):  
Xinying Zhang ◽  
Yingying Qu ◽  
Xuesen Fan ◽  
Xia Wang ◽  
Jianji Wang
Keyword(s):  
Ionic Liquid ◽  
High Efficiency ◽  
Reaction Medium ◽  
Environmentally Benign ◽  
Pyrimidine Nucleoside ◽  
Reaction Conditions ◽  
Operation Process ◽  
Antiviral Activities ◽  
Benign Nature ◽  
High Yields

The utilisation of an ionic liquid-[bmim][BF4] as both reaction medium and promoter for the reaction between aldehyde and 4-hydroxy-6-methylpyran-2-one is described. Without any added catalyst, this reaction was realised efficiently to give arylbispyranylmethane derivatives in high yields. Alternatively, when this reaction was carried out in the presence of acetic anhydride, fused pyran derivatives were obtained. These two novel procedures have advantages such as an environmentally benign nature, high efficiency, simple operation process and mild reaction conditions. As an application, these procedures were used in the preparation of novel 5-substituted pyrimidine nucleoside derivatives with potential antiviral activities.

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