In Melting Points We Trust: A Review on the Misguiding Characterization of Multicomponent Reactions Adducts and Intermediates DOI Creative Commons
Brenno A. D. Neto, Pedro S. Beck, Jenny E. P. Sorto

и другие.

Molecules, Год журнала: 2022, Номер 27(21), С. 7552 - 7552

Опубликована: Ноя. 4, 2022

We discuss herein the problems associated with using melting points to characterize multicomponent reactions' (MCRs) products and intermediates. Although surprising, it is not rare find articles in which these MCRs final adducts (or their intermediates) are characterized solely by comparing those available from other reports. A brief survey among specialized highlights serious obvious this practice since, for instance, cases found as many 25 quite contrasting have been attributed very same MCR adduct. Indeed, seems logical assume that inherent non-confirmatory nature of could be vastly misleading a protocol structural confirmation, but still publications (also Q1 Q2 quartiles) insist on it. This procedure contradicts best practices organic synthesis, fraught limitations conclusions published field. The drawbacks indeed misguided advances. therefore suggest some precautions aimed at avoiding future confusions.

Язык: Английский

Multicomponent Reaction-Assisted Drug Discovery: A Time- and Cost-Effective Green Approach Speeding Up Identification and Optimization of Anticancer Drugs DOI Open Access
Giovanni Graziano, Angela Stefanachi, Marialessandra Contino

и другие.

International Journal of Molecular Sciences, Год журнала: 2023, Номер 24(7), С. 6581 - 6581

Опубликована: Апрель 1, 2023

Multicomponent reactions (MCRs) have emerged as a powerful strategy in synthetic organic chemistry due to their widespread applications drug discovery and development. MCRs are flexible transformations which three or more substrates react form structurally complex products with high atomic efficiency. They being increasingly appreciated highly exploratory evolutionary tool by the medicinal community, opening door sustainable, cost-effective rapid synthesis of biologically active molecules. In recent years, MCR-based strategies found extensive application field discovery, several anticancer drugs been synthesized through MCRs. this review, we present an overview representative literature examples documenting different approaches development new drugs.

Язык: Английский

Процитировано

44

Ultra-highly efficient adsorbent for CO2 capture from air by directional deprotonation regulation of MOFs-based amine grafting DOI
Tao Wang, Fengsheng Liu, Wenjing Tang

и другие.

Chemical Engineering Journal, Год журнала: 2024, Номер 490, С. 151426 - 151426

Опубликована: Апрель 23, 2024

Язык: Английский

Процитировано

7

Catalytic Transformation of Carbohydrates into Renewable Organic Chemicals by Revering the Principles of Green Chemistry DOI Creative Commons
Saikat Dutta

ACS Omega, Год журнала: 2024, Номер 9(25), С. 26805 - 26825

Опубликована: Июнь 12, 2024

Adherence to the principles of green chemistry in a biorefinery setting ensures energy efficiency, reduces consumption materials, simplifies reactor design, and rationalizes process parameters for synthesizing affordable organic chemicals desired functional efficacy ingrained sustainability. The metrics facilitate assessing relative merits demerits alternative synthetic pathways targeted product(s). This work elaborates on how has emerged as transformative framework inspired innovations toward catalytic conversion biomass-derived carbohydrates into fuels, chemicals, polymers. Specific discussions have been incorporated judicious selection feedstock, reaction parameters, reagents (stoichiometric or catalytic), other auxiliaries obtain product(s) selectivity yield. prospects carbohydrate-centric emphasized research avenues proposed eliminate remaining roadblocks. analyses presented this review will steer developing superior strategies processes envisaging sustainable bioeconomy centered carbohydrates.

Язык: Английский

Процитировано

3

Solvent Dependent Competitive Mechanisms for the Ugi Multicomponent Reaction: A Joint Theoretical and Experimental Study in the α-Acyl Aminocarboxamides vs α-Amino Amidines Formation DOI
Marcelo H. R. Carvalho,

João P. R. S. Ribeiro,

Pedro P. de Castro

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(16), С. 11007 - 11020

Опубликована: Авг. 4, 2022

A synthetic protocol for the preparation of α-acyl aminocarboxamides and α-amino amidines is proposed. The selectivity toward each these two possible products was tuned by simple modifications reaction conditions. broad scope presented, allowing access to desired in up 87% (Ugi adduct) 93% (α-amino amidine). Theoretical calculations were carried out, analysis led proposal a new mechanistic pathway Ugi reaction, which methanol acts not only as solvent but also reagent. High-resolution (tandem) mass spectrometry experiments allowed detection characterization key intermediate associated with this alternative pathway, thus supporting theoretical proposal.

Язык: Английский

Процитировано

10

One-Pot Multicomponent Reactions in Deep Eutectic Solvents DOI
Aslıhan Ayvaz, Sinem G. Demirbas, A. Demirbaş

и другие.

Current Organic Chemistry, Год журнала: 2023, Номер 27(7), С. 585 - 620

Опубликована: Апрель 1, 2023

Abstract: The increasing environmental pollution and its detrimental impact on the ecosystem made scientists develop new chemical strategies involving eco-friendly chemicals, solvents, catalysts, atom-economical procedures, alternative energy sources. Among these, deep eutectic solvents (DESs) are primarily low-melting mixtures of quaternary ammonium salt hydrogen-bond acceptors. Low toxicity, easy preparation, low cost, biodegradability, vapor pressure, recyclability main advantages DESs. Multicomponent reactions (MCRs) efficient procedures for generating libraries with high structural complexity. MCRs can give one product from at least three components in a single operation bond-forming efficiency, shortness, diversity. Compared conventional methodologies, diversity, convergent atom economic character, applicability one-pot operation, accessibility to complex molecules, minimized waste formation, selectivity multicomponent reactions. application not only simplifies but also displays more positive effects protection ecosystem.

Язык: Английский

Процитировано

5

Revisiting Biginelli-like reactions: solvent effects, mechanisms, biological applications and correction of several literature reports DOI
Pedro S. Beck, Arthur G. Leitão,

Yasmin B. Santana

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(18), С. 3630 - 3651

Опубликована: Янв. 1, 2024

This study critically reevaluates reported Biginelli-like reactions using a Kamlet-Abboud-Taft-based solvent effect model. Surprisingly, structural misassignments were discovered in certain multicomponent reactions, leading to the identification of pseudo three-component derivatives instead expected MCR adducts. Attempts replicate literature conditions failed, prompting reconsideration described MCRs and proposed mechanisms. Electrospray ionization (tandem) mass spectrometry, NMR, melting points, elemental analyses single-crystal X-ray analysis exposed inaccuracies allowed for proposition complete catalytic cycle. Biological investigations both pure "contaminated" revealed distinctive features assessed bioassays. A new cellular action mechanism was unveiled one obtained adduct, suggesting similarity with known dihydropyrimidinone Monastrol as Eg5 inhibitors, disrupting mitosis by forming monoastral mitotic spindles. Docking studies RMSD supported this hypothesis. The findings herein underscore necessity critical reexamination potential corrections assignments several reports. work emphasizes significance rigorous characterization evaluation synthetic chemistry, urging careful reassessment synthesis biological activities associated these compounds.

Язык: Английский

Процитировано

1

In Melting Points We Trust: A Review on the Misguiding Characterization of Multicomponent Reactions Adducts and Intermediates DOI Creative Commons
Brenno A. D. Neto, Pedro S. Beck, Jenny E. P. Sorto

и другие.

Molecules, Год журнала: 2022, Номер 27(21), С. 7552 - 7552

Опубликована: Ноя. 4, 2022

We discuss herein the problems associated with using melting points to characterize multicomponent reactions' (MCRs) products and intermediates. Although surprising, it is not rare find articles in which these MCRs final adducts (or their intermediates) are characterized solely by comparing those available from other reports. A brief survey among specialized highlights serious obvious this practice since, for instance, cases found as many 25 quite contrasting have been attributed very same MCR adduct. Indeed, seems logical assume that inherent non-confirmatory nature of could be vastly misleading a protocol structural confirmation, but still publications (also Q1 Q2 quartiles) insist on it. This procedure contradicts best practices organic synthesis, fraught limitations conclusions published field. The drawbacks indeed misguided advances. therefore suggest some precautions aimed at avoiding future confusions.

Язык: Английский

Процитировано

4