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Molecules
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How and Why to Investigate Multicomponent Reactions Mechanisms
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How and Why to Investigate Multicomponent Reactions Mechanisms

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (29 February 2024) | Viewed by 8764

Special Issue Editor

Prof. Dr. Brenno A.D. Neto

E-Mail Website
Guest Editor
Intituto de Química, Universidade de Brasília, Brasilia, Brazil
Interests: reaction mechanisms; multicomponent reactions; functional chromophores; solvent effects; catalysis

Special Issue Information

Dear Colleagues,

This Special Issue focuses on the elucidation of multicomponent reactions (MCRs) mechanisms, the effects of catalysis over reaction pathways and methodologies applied in the elucidation of such tricky reactions. The possibility of two or more reaction routes usually observed in MCRs, with several common intermediates formed at different stages, and the challenges noted to select one of these routes are discussed in this Special Issue.

Manuscript formats adopted by Molecules may additionally include the following types of papers: articles, reviews, communications, brief reports, etc.

Prof. Dr. Brenno A.D. Neto
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • reaction mechanism
  • mass spectrometry
  • multicomponent reaction
  • NMR
  • reaction route
  • reaction intermediate
  • kinetic

Published Papers (4 papers)

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Research

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10 pages, 2780 KiB  
Article
Evidence of Isomerization in the Michael-Type Thiol-Maleimide Addition: Click Reaction between L-Cysteine and 6-Maleimidehexanoic Acid
by Víctor Alfonso Niño-Ramírez, Diego Sebastián Insuasty-Cepeda, Zuly Jenny Rivera-Monroy and Mauricio Maldonado
Molecules 2022, 27(16), 5064; https://doi.org/10.3390/molecules27165064 - 09 Aug 2022
Cited by 2 | Viewed by 2380
Abstract
The reaction between L-cysteine (Cys) and 6-maleimidohexanoic acid (Mhx) in an aqueous medium at different levels of pH was analyzed via RP-HPLC, finding the presence of two reaction products throughout the evaluated pH range. By means of solid-phase extraction (SPE), it was possible [...] Read more.
The reaction between L-cysteine (Cys) and 6-maleimidohexanoic acid (Mhx) in an aqueous medium at different levels of pH was analyzed via RP-HPLC, finding the presence of two reaction products throughout the evaluated pH range. By means of solid-phase extraction (SPE), it was possible to separate the products and obtain isolated profiles enriched up to 80%. The products were analyzed individually through mass spectrometry, DAD-HPLC, NMR 1H, 13C, and two-dimensional evidence of isomerization between the hydrogen atoms of the α-amino and the thiol group present in the cysteine. Thus, it was concluded that the products obtained corresponded to a mixture of the isomer Cys-S-Mhx, where the adduct is formed by a thioether bond, and the isomer Cys-NH-Mhx, in which the union is driven by the amino group. We consider that the phenomenon of isomerization is an important finding, since it has not previously been reported for this reaction. Full article
(This article belongs to the Special Issue How and Why to Investigate Multicomponent Reactions Mechanisms)
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8 pages, 1361 KiB  
Article
Hf(OTf)4-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones
by Zhen-Zhen Chen, Dong-Zhao Yang, Ying-Ying Dong, Mei Chi, Shou-Zhi Pu and Qi Sun
Molecules 2022, 27(3), 1122; https://doi.org/10.3390/molecules27031122 - 08 Feb 2022
Cited by 2 | Viewed by 1752
Abstract
Hafnium(IV) triflate (Hf(OTf)4) has been identified as a potent catalyst for the direct three-component synthesis of β-carbamate ketones. This new method, featuring a low catalyst loading, fast reaction rate, and solvent-free conditions, provided facile access to a diversity of carbamate-protected Mannich [...] Read more.
Hafnium(IV) triflate (Hf(OTf)4) has been identified as a potent catalyst for the direct three-component synthesis of β-carbamate ketones. This new method, featuring a low catalyst loading, fast reaction rate, and solvent-free conditions, provided facile access to a diversity of carbamate-protected Mannich bases. A mechanistic investigation indicated that the three-component reaction proceeds via sequential aldol condensation and aza-Michael addition, but not the Mannich-type pathway. Full article
(This article belongs to the Special Issue How and Why to Investigate Multicomponent Reactions Mechanisms)
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Scheme 1

11 pages, 1553 KiB  
Article
An Improved Approach for Practical Synthesis of 5-Hydroxymethyl-2′-deoxycytidine (5hmdC) Phosphoramidite and Triphosphate
by Dong-Zhao Yang, Zhen-Zhen Chen, Mei Chi, Ying-Ying Dong, Shou-Zhi Pu and Qi Sun
Molecules 2022, 27(3), 749; https://doi.org/10.3390/molecules27030749 - 24 Jan 2022
Cited by 2 | Viewed by 2701
Abstract
5-Hydroxymethyl-2′-deoxycytidine (5hmdC) phosphoramidite and triphosphate are important building blocks in 5hmdC-containing DNA synthesis for epigenetic studies. However, efficient and practical methods for the synthesis of these compounds are still limited. The current research provides an intensively improved synthetic method that enables the preparation [...] Read more.
5-Hydroxymethyl-2′-deoxycytidine (5hmdC) phosphoramidite and triphosphate are important building blocks in 5hmdC-containing DNA synthesis for epigenetic studies. However, efficient and practical methods for the synthesis of these compounds are still limited. The current research provides an intensively improved synthetic method that enables the preparation of commercially available cyanoethyl-protected 5hmdC phosphoramidite with an overall yield of 39% on 5 g scale. On the basis of facile and efficient accesses to cyanoethyl protected-5hmdU and 5hmdC intermediates, two efficient synthetic routes for 5hmdC triphosphate were also developed. Full article
(This article belongs to the Special Issue How and Why to Investigate Multicomponent Reactions Mechanisms)
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Review

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18 pages, 3226 KiB  
Review
In Melting Points We Trust: A Review on the Misguiding Characterization of Multicomponent Reactions Adducts and Intermediates
by Brenno A. D. Neto, Pedro S. Beck, Jenny E. P. Sorto and Marcos N. Eberlin
Molecules 2022, 27(21), 7552; https://doi.org/10.3390/molecules27217552 - 04 Nov 2022
Cited by 1 | Viewed by 1483
Abstract
We discuss herein the problems associated with using melting points to characterize multicomponent reactions’ (MCRs) products and intermediates. Although surprising, it is not rare to find articles in which these MCRs final adducts (or their intermediates) are characterized solely by comparing melting points [...] Read more.
We discuss herein the problems associated with using melting points to characterize multicomponent reactions’ (MCRs) products and intermediates. Although surprising, it is not rare to find articles in which these MCRs final adducts (or their intermediates) are characterized solely by comparing melting points with those available from other reports. A brief survey among specialized articles highlights serious and obvious problems with this practice since, for instance, cases are found in which as many as 25 quite contrasting melting points have been attributed to the very same MCR adduct. Indeed, it seems logical to assume that the inherent non-confirmatory nature of melting points could be vastly misleading as a protocol for structural confirmation, but still many publications (also in the Q1 and Q2 quartiles) insist on using it. This procedure contradicts best practices in organic synthesis, and articles fraught with limitations and misleading conclusions have been published in the MCRs field. The drawbacks inherent to this practice are indeed serious and have misguided MCRs advances. We therefore suggest some precautions aimed at avoiding future confusions. Full article
(This article belongs to the Special Issue How and Why to Investigate Multicomponent Reactions Mechanisms)
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