Glutarimide Alkaloids Through Multicomponent Reaction Chemistry

Konstantinidou, Markella; Kurpiewska, Katarzyna; Kalinowska‐Tłuścik, Justyna; Dömling, Alexander

doi:10.1002/ejoc.201801276

Cited by 18 publications

(8 citation statements)

References 24 publications

(25 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the literature, a large amount of information about approaches to the synthesis of (–)-julocrotine can be found. 47 Thus, in the publication of 2018 48 for the production of (–)-julocrotine and its analogues, a four-component Ugi reaction between (2-isocyanoethyl)benzene ( 58 ), isobutyric acid ( 59 ), methyl-4-oxobutanoate ( 60 ), and ( R )-1-(4-methoxyphenyl)ethanamine ( 61 ) was employed (Scheme 22 ). At the same time, it was found that the optimal conditions for this reaction are the use of 2,2,2-trifluoroethanol (TFE) as a solvent with a concentration of reagents of 1 mol/L.…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

“…In the literature, a large amount of information about approaches to the synthesis of (-)-julocrotine can be found. 47 Thus, in the publication of 2018 48 for the production of (-)-julocrotine and its analogues, a four-component Ugi reaction between (2-isocyanoethyl)benzene (58), isobutyric acid (59), methyl-4-oxobutanoate (60), and (R)-1-(4-methoxyphe-…”

Section: Scheme 21 Synthesis Of a Drug Used Against Breast Cancer (Ag...mentioning

confidence: 99%

See 1 more Smart Citation

Preparation of N- and C-Functionally-Substituted Glutarimides: A Review

Trukhanova¹,

Chernov²,

Kuvaeva³

et al. 2023

Synthesis

View full text Add to dashboard Cite

Six-membered heterocyclic systems such as glutarimides are widely used in medicinal chemistry. The glutarimide skeleton is found in many commercially available pharmaceuticals due to a wide range of bioactivity. The preparation of C,N-highly functionalized glutarimides is an important topic in modern organic synthesis, since it reveals the ability to build a more complex system and thus expands the range of various drugs. This review describes approaches to the synthesis of N- and C-functionally-substituted glutarimides presented in the literature from 2005 to 2022. Options for the enantioselective synthesis of spiroglutarimides, the use of organocatalysis in the synthesis of glutarimides, and optimization of the synthesis of already known pharmaceuticals are described.1 Introduction2 Michael Addition2.1 Preparation of Glutarimides from Substituted Acrylamides and 1,3-Bielectrophiles2.2 Preparation of Glutarimides by the Reaction of Acetamide and α,β-Unsaturated Carbonyl Compounds2.2.1 Preparation of Glutarimides by the Reaction of Acetamide Derivatives and Acrolein Derivatives2.2.2 Preparation of Spiroglutarimides by the Reaction of Acetamide Derivatives and Bromacrolein Derivatives2.2.3 Preparation of Spiroglutarimides by the Reaction of Acetamide Derivatives and Acryloyl Cyanide Derivatives2.2.4 Preparation of Substituted Glutarimides Using Ytterbium Salts2.3 Michael Addition/Intramolecular Transacylation2.4 Preparation of Glutarimides from Baylis–Hillman Adducts3 Multicomponent Reactions4 Conclusion

show abstract

Section: Multicomponent Reactionsmentioning

confidence: 99%

Section: Scheme 21 Synthesis Of a Drug Used Against Breast Cancer (Ag...mentioning

confidence: 99%

Preparation of N- and C-Functionally-Substituted Glutarimides: A Review

Trukhanova¹,

Chernov²,

Kuvaeva³

et al. 2023

Synthesis

View full text Add to dashboard Cite

show abstract

“…Multi-component reactions (MCRs) have regarded as essential tools for the preparation of biologically active heterocyclic compounds because of their productivity, convergence, simple procedures, and easy execution [ 1 ]. The development of MCRs and their applications for the one-pot synthesis of various useful heterocyclic compounds are of remarkable interest in the running research articles [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

One-pot multi-component synthesis of new bis-pyridopyrimidine and bis-pyrimidoquinolone derivatives

Masoumi

Bayat

Hosseini

2020

Heliyon

View full text Add to dashboard Cite

A variety of bis-heterocycles such as bis(pyrimido[4,5- b ]quinolone), bis(chromeno[3′,4':5,6]pyrido[2,3- d ]pyrimidine), bis(pyrido[2,3- d :6,5- d' ]dipyrimidine), and bis(benzo[ g ]pyrimido[4,5- b ]quinolone) derivatives were synthesized via one-pot, multi-component reaction of various 6-aminouracils or 6-aminothiouracils, terephthalaldehyde, and CH-acids such as 4-hydroxycoumarin, dimedone, 2-hydroxy-1,4-naphthoquinone, barbituric acid, and thiobarbituric acid in EtOH as a solvent at reflux. The mild conditions, fast rate of reaction, absence of catalyst, different functional group compatibility, simple operation and work-up involving no chromatographic process, are worth mentioning.

show abstract

“…14 Therefore, the design of novel MCRs has attracted great attention from synthetic organic chemists. [15][16][17][18][19][20] Chromenes and their fused analogues are a group of biologically active molecules occurring extensively in nature with a wide range of molecular modications. 21 Among them benzochromenes are one of the privileged scaffolds with a medicinal pharmacophore such as antibacterial, 22 antimicrobial, 23 antitumor, 24 and anti-inammatory.…”

Section: Introductionmentioning

confidence: 99%

Rapid and catalyst free synthesis of new bis(benzo[g]chromene) and bis(pyrano[3,2-c]chromene) derivatives and optimization of reaction conditions using response surface methodology

2019

View full text Add to dashboard Cite

Rapid and catalyst free synthesis of new bis(benzo [g]chromene) and bis(pyrano[3,2-c]chromene) derivatives and optimization of reaction conditions using response surface methodology † Fahimeh Sadat Hosseini, Mohammad Bayat * and Milad Afsharnezhad 4,4 0 -(1,4-phenylene)bis(2-(alkylamino)-3-nitro-4H-benzo[g]chromene-5,10-dione) and 4,4 0 -(1,4phenylene)bis(2-(alkylamino)-3-nitropyrano[3,2-c]chromen-5(4H)-one) derivatives are synthesized by a one-pot, multi-component reaction of N-alkyl-1-(methylthio)-2-nitroethenamine (derived from the reaction of various amines and 1,1-bis(methylthio)-2-nitroethene) with terephthalaldehyde or isophthalaldehyde, and 2-hydroxy-1,4-naphthoquinone or 4-hydroxycoumarin in EtOH/H 2 O (85 : 15) as the solvent at 89 C. Response surface methodology (RSM) is used to investigate the effect of reaction temperature and water content of aqueous ethanol on the product yields and reaction time. The notable features of this work are the optimization of reaction conditions with minimal experiments, absence of catalyst, good yields, simple work-up and the non-chromatographic purification of products. ; Tel: +98 28 33780040 † Electronic supplementary information (ESI) available. See a Various amines (2 mmol), 1,1-bis(methylthio)-2-nitroethene (2 mmol), phthalaldehyde (1 mmol), 2-hydroxy-1,4-naphthoquinone (2 mmol) and 4hydroxycumarin (2 mmol) were used. The reactions were run in EtOH/H 2 O (85 : 15) at 89 C, without any catalyst.Scheme 5 Proposed mechanism for the synthesis of product 6.This journal is

show abstract

Glutarimide Alkaloids Through Multicomponent Reaction Chemistry

Cited by 18 publications

References 24 publications

Preparation of N- and C-Functionally-Substituted Glutarimides: A Review

Preparation of N- and C-Functionally-Substituted Glutarimides: A Review

One-pot multi-component synthesis of new bis-pyridopyrimidine and bis-pyrimidoquinolone derivatives

Rapid and catalyst free synthesis of new bis(benzo[g]chromene) and bis(pyrano[3,2-c]chromene) derivatives and optimization of reaction conditions using response surface methodology

Contact Info

Product

Resources

About