scholarly journals The Alternative Route to Enantiopure Multicomponent Reaction Products: Biocatalytic or Organocatalytic Enantioselective Production of Inputs for Multicomponent Reactions (Eur. J. Org. Chem. 10/2014)

2014 ◽  
Vol 2014 (10) ◽  
pp. n/a-n/a ◽  
Author(s):  
Luca Banfi ◽  
Andrea Basso ◽  
Lisa Moni ◽  
Renata Riva
Keyword(s):  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Alternative Route ◽  
Reaction Products

scholarly journals Synthesis of depsipeptides via isocyanide-based consecutive Bargellini/Passerini multicomponent reactions

SynOpen ◽  
2021 ◽  
Author(s):  
Hassan Farhid ◽  
Mohammad Mahdi Rostami ◽  
Ahmad Shaabani ◽  
Behrouz Notash
Keyword(s):  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Flexible Structures ◽  
Amide Bond ◽  
Environmentally Benign ◽  
Reaction Products ◽  
Reaction Conditions ◽  
New Class ◽  
High Yields ◽  
Straightforward Approach

An efficient and straightforward approach has been established for the preparation of new class of depsipeptide structures via isocyanide-based consecutive Bargellini/Passerini multicomponent reactions. 3-Carboxamido-isobutyric acids bearing an amide bond were supplied via Bargellini multicomponent reaction from isocyanides, acetone, and chloroform in the presence of sodium hydroxide. Next, via the Passerini multicomponent reaction strategy, a new class of depsipeptides was synthesized using the Bargellini reaction products, isocyanides, and aldehydes under environmentally benign reaction conditions. The prepared depsipeptides have more flexible structures than their pseudopeptidic analogs. Using cheap and readily available starting materials, mild reaction conditions, simple procedures, and high yields are the advantages of the present strategy.

scholarly journals An evaluation of credentials of a multicomponent reaction for the synthesis of isothioureas through the use of a holistic CHEM21 green metrics toolkit

2017 ◽  
Vol 19 (1) ◽  
pp. 249-258 ◽  
Author(s):  
S. Abou-Shehada ◽  
P. Mampuys ◽  
B. U. W. Maes ◽  
J. H. Clark ◽  
L. Summerton
Keyword(s):  
Organic Compounds ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Materials Used

Multicomponent reactions (MCRs) are considered green and material efficient methods for the synthesis of organic compounds, however very few studies have investigated the metrics of the upstream processes involved to achieve the starting materials used in these reactions.

Pot, atom and step-economic (PASE) synthesis of medicinally relevant spiro[oxindole-3,4′-pyrano[4,3-b]pyran] scaffold

2016 ◽  
Vol 22 (1) ◽  
pp. 11-15 ◽  
Author(s):  
Michail N. Elinson ◽  
Fedor V. Ryzhkov ◽  
Victor A. Korolev ◽  
Mikhail P. Egorov
Keyword(s):  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Large Scale ◽  
Potassium Fluoride ◽  
Environmentally Benign ◽  
Anti Hiv

AbstractFast (3 min) pot, atom and step economics (PASE) potassium fluoride catalyzed multicomponent reaction of isatins, malononitrile and 4-hydroxy-6-methyl-2H-pyran-2-one results in efficient formation of substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans in 92–96% yields. The developed ‘on-solvent’ approach to the substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans – the pharmacologically perspective substances with known antiviral, antileishmanial, anticonvulsant and anti-HIV activities – is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast and environmentally benign synthetic concept for the multicomponent reactions strategy.

scholarly journals Synthesis of Biologically Active Molecules through Multicomponent Reactions

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 505 ◽  
Author(s):  
Daniel Insuasty ◽  
Juan Castillo ◽  
Diana Becerra ◽  
Hugo Rojas ◽  
Rodrigo Abonia
Keyword(s):  
Multicomponent Reaction ◽  
Biological Property ◽  
Multicomponent Reactions ◽  
Organic Molecules ◽  
Biological Activities ◽  
Biologically Active ◽  
Vast Number ◽  
Key Points ◽  
Reported Data ◽  
Synthetic Approaches

Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.

scholarly journals Concise Synthesis of Macrocycles by Multicomponent Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (05) ◽  
pp. 1027-1038 ◽  
Author(s):  
Alexander Dömling ◽  
Eman Abdelraheem ◽  
Samad Khaksar
Keyword(s):  
Amino Acid ◽  
Multicomponent Reaction ◽  
Ring Opening ◽  
Multicomponent Reactions ◽  
Reaction Pathway ◽  
Ring Closure ◽  
Side Chains ◽  
Reaction Sequence ◽  
Cyclic Anhydride

A short reaction pathway was devised to synthesize a library of artificial 18–27-membered macrocycles. The five-step reaction sequence involves ring opening of a cyclic anhydride with a diamine, esterification, coupling with an amino acid isocyanide, saponification, and, finally, macro-ring closure using an Ugi or, alternatively, a Passerini multicomponent reaction. Three out of the five steps allow for the versatile introduction of linker elements, side chains, and substituents with aromatic, heteroaromatic, and aliphatic character. The versatile pathway is described for 15 different target macrocycles on a mmol scale. Artificial macrocycles have recently become of great interest due to their potential to bind to difficult post-genomic targets.

Cyclopropylcarbinyl-oxo-carbonium Ions. Part VI. Synthesis and Chemistry of an Epimeric Pair of Homoallyl Iodides (3-Iodomethyl Glycals)

1972 ◽  
Vol 50 (18) ◽  
pp. 2919-2927 ◽  
Author(s):  
Bert Fraser-Reid ◽  
Bruno Radatus
Keyword(s):  
Transition State ◽  
Major Product ◽  
Alternative Route ◽  
Allylic Rearrangement ◽  
Reaction Products ◽  
Primary Reaction ◽  
Methylene Iodide ◽  
Carbonium Ions ◽  
Synthetic Sequence ◽  
Zinc Iodide

The homoallyl iodide 4,6-O-benzylidene-1,2,3-trideoxy-D-ribo-hex-1-enopyranose, 4, is the second major product from Simmons–Smith reaction of methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopy-ranoside, 6α. The major product is the cyclopropyl glycoside 7α, which when treated separately with the Simmons–Smith reagents furnishes an 85% yield of 4. The mechanism of this transformation is investigated. It is not simply a Lewis-catalyzed iodinolysis since zinc iodide in a variety of solvents does not convert 7α to 4. Methylene iodide is essential, as is the organo-zincate complex, operative in Simmons–Smith reactions.The 3-epimer of the homoallyl iodide 4, i.e. 4,6-O-benzylidene-1,2,3-trideoxy-D-arbino-hex-1-enopyranose, 5, is produced in only 0.9% yield in the methylenation of the anomeric olefinic glycoside, 6β. The low yield is attributable to the extensive anomerization experienced by 6β itself, and by the primary reaction products. This leads to a plethora of compounds including both epimeric homoallyl iodides 4 and 5.In order to get it all together, the homoallyl iodide 4 is transformed into its epimer 5 by an unambiguous synthetic sequence. Some of the intermediates in this sequence are polyfunctional molecules of considerable synthetic potential.The possibility of an alternative route to compound 4 directly from the olefinic glycoside 6α is discussed. Coordination of the methoxyl oxygen of 6α to the organo-zincate complex could achieve an ideal SNi transition state in which [Formula: see text] is delivered at C-3 with synchronous departure of the methoxyl group. This mechanism, called the "reverse" allylic rearrangement for reasons outlined in the text, is discussed.

scholarly journals Synthesis of Medicinally Important Quinazolines and Their Derivatives: A Review

2020 ◽  
Vol 14 (1) ◽  
pp. 108-121
Author(s):  
Sulochana Sharma ◽  
Kailash Sharma ◽  
Sakshi Pathak ◽  
Mahendra Kumar ◽  
Praveen Kumar Sharma
Keyword(s):  
Clinical Trials ◽  
Ionic Liquids ◽  
Multicomponent Reactions ◽  
Chemical Compounds ◽  
Review Article ◽  
High Yield ◽  
Pharmacological Properties ◽  
Reaction Products ◽  
Microwave Irradiations ◽  
High Yields

The study of biodynamic heterosystems has proved to be the most attractive and useful for the development of potential drugs with superior properties and works effectively for the treatment of a variety of diseases, including pandemic ones. Out of the thousand biodynamic heterosystems, the quinazoline heterosystem is one that exhibits wide-ranging biological and pharmacological properties. Synthesis of potential medicinal material is comparatively challenging and needed enough time for clinical trials, testing, permissions for concerned authorities, production and supply. Therefore, researchers usually focused on novel methods incorporated with a high yield of previously approved chemical compounds. This present review article has focused on the synthesis of medicinally important quinazolines and their derivatives, which produce reaction products in less time with high yields, including more attention with eco-friendly green synthesis approaches incorporating multicomponent reactions (MCR), ionic liquids and microwave irradiations.

scholarly journals Ecofriendly and Facile One-Pot Multicomponent Synthesis of Thiopyrimidines under Microwave Irradiation

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Biswa Mohan Sahoo ◽  
B. V. V. Ravi Kumar ◽  
Jnyanaranjan Panda ◽  
S. C. Dinda
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Spectral Data ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Heating Method ◽  
Green Protocol ◽  
Drug Molecules

A rapid, improved, and ecofriendly synthesis of thiopyrimidines is carried out via one-pot multicomponent reaction of ethylcyanoacetate, substituted benzaldehydes, and thiourea in presence of ethanolic K2CO3 using microwave irradiation heating method. Excellent yields, shorter reaction time, and easy workup are the major advantageous features of this green protocol. So the application of multicomponent reactions involves the combination of multiple starting materials with different functional groups leading to the highly efficient and environmentally friendly construction of multifunctional drug molecules. The structures of the newly synthesized products were assigned on the basis of IR and 1HNMR spectral data.

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