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Recent Advances in Domino Reactions
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Recent Advances in Domino Reactions

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

Deadline for manuscript submissions: closed (31 December 2024) | Viewed by 4402

Special Issue Editors

Dr. Tecla Gasperi

E-Mail Website
Guest Editor
Department of Science, University Roma Tre, Via della Vasca Navale 79, I-00146 Roma, Italy
Interests: organocatalysis; organic synthesis; materials chemistry/science; medicinal chemistry; drug delivery system; natural products
Dr. Maria Gessica Ciulla

E-Mail Website
Guest Editor Assistant
Department of Chemistry, University of Milan, 20133 Milan, Italy
Interests: medicinal chemistry; drug discovery; organic synthesis; natural products chemistry; materials chemistry/science
Dr. Miguel Garcia-Castro

E-Mail Website
Guest Editor Assistant
Department of Organic Chemistry, Faculty of Sciences, University of Malaga, 29071 Málaga, Spain
Interests: natural product; organic chemistry; new drug discovery; synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue is dedicated to highlighting the most recent developments in the field of domino reactions in organic synthesis. The charm of domino reactions is the overcoming of the long and multistep synthesis routes to reach products with high chemo-, regio-, and stereoselectivity (e.g., natural products).

Domino reactions yield the production of a large number of molecules in a single step and may serve for the development of compound libraries in drug discovery and chemical biology research. In most cases, these synthetic strategies meet more recent and non-standard procedures, including microwave irradiation, solid-phase synthesis, alternative reaction media, and the use of fluorescent reagents.

The aim of this Special Issue is to attract organic synthetic chemists, along with medicinal chemists and biologists, to showcase the advances and relative applications in the realizable production of complex molecules thanks to cascade synthesis and domino reactions, as well as provide answers to the challenges of modern organic chemistry.

Dr. Tecla Gasperi
Guest Editor

Dr. Maria Gessica Ciulla
Dr. Miguel García-Castro
Guest Editor Assistant

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

  • domino reactions
  • tandem
  • cascade
  • scaffold diversity
  • enantioselectivity
  • asymmetry
  • structural complexity

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Published Papers (4 papers)

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Research

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14 pages, 1911 KiB  
Article
tert-Butyl Hypochlorite: A Reagent for the Synthesis of Chlorinated Oxindole and Indole Derivatives
by Chun-Yan Liu, Xia Chen, Hai-Long Liu, Nan Wang and Xiao-Yu Zhou
Molecules 2025, 30(1), 102; https://doi.org/10.3390/molecules30010102 - 30 Dec 2024
Viewed by 403
Abstract
tert-Butyl hypochlorite was employed as a versatile reagent for chlorooxidation of indoles, chlorination of 2-oxindoles, and decarboxylative chlorination of the indole-2-carboxylic acids. Four types of products including 2-chloro-3-oxindoles, 2,2-dichloro-3-oxindoles, 3,3-dichloro-2-oxindoles, and 2,3-dichloroindoles could be selectively obtained in moderate to excellent yields by [...] Read more.
tert-Butyl hypochlorite was employed as a versatile reagent for chlorooxidation of indoles, chlorination of 2-oxindoles, and decarboxylative chlorination of the indole-2-carboxylic acids. Four types of products including 2-chloro-3-oxindoles, 2,2-dichloro-3-oxindoles, 3,3-dichloro-2-oxindoles, and 2,3-dichloroindoles could be selectively obtained in moderate to excellent yields by switching the substrates. Various synthetically useful functional groups, such as halogen atoms, cyano, nitro, and methoxycarbonyl groups, remain intact during the reactions. Notable features of the approach include the universality of the starting materials, the mild reaction conditions, and the experimental simplicity. Full article
(This article belongs to the Special Issue Recent Advances in Domino Reactions)
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16 pages, 1831 KiB  
Article
Expedient Synthesis of Substituted Thieno[3,2-b]thiophenes and Selenopheno[3,2-b]selenophenes Through Cascade Cyclization of Alkynyl Diol Derivatives
by Yingqi Feng, Xuelin Zhang, Ziqing He, Miaoshan Zhao, Lu Chen, Yibiao Li and Xiai Luo
Molecules 2024, 29(23), 5507; https://doi.org/10.3390/molecules29235507 - 21 Nov 2024
Viewed by 569
Abstract
Thieno[3,2-b]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-b]thiophene and selenopheno[3,2-b]selenophenes in moderate to good yields via [...] Read more.
Thieno[3,2-b]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-b]thiophene and selenopheno[3,2-b]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I2/Na2S2O3 or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials. Full article
(This article belongs to the Special Issue Recent Advances in Domino Reactions)
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19 pages, 2565 KiB  
Article
2,5-Di-tert-butyl-2,5-diethylpyrrolidine-1-oxyls: Where Is a Reasonable Limit of Sterical Loading for Higher Resistance to Reduction?
by Irina F. Zhurko, Sergey A. Dobrynin, Yurii I. Glazachev, Yuri V. Gatilov and Igor A. Kirilyuk
Molecules 2024, 29(3), 599; https://doi.org/10.3390/molecules29030599 - 25 Jan 2024
Cited by 1 | Viewed by 1456
Abstract
The pyrrolidine nitroxides with four bulky alkyl substituents adjacent to the N–O∙ group demonstrate very high resistance to reduction with biogenic antioxidants and enzymatic systems. This makes them valuable molecular tools for studying the structure and functions of biomolecules directly in a living [...] Read more.
The pyrrolidine nitroxides with four bulky alkyl substituents adjacent to the N–O∙ group demonstrate very high resistance to reduction with biogenic antioxidants and enzymatic systems. This makes them valuable molecular tools for studying the structure and functions of biomolecules directly in a living cell and for functional EPR and NMR tomography in vivo. The first example of highly strained pyrrolidine nitroxides with both ethyl and tert-butyl groups at each of the α-carbon atoms of the nitroxide moiety with cis-configuration of the tert-butyl groups was prepared using a three-component domino reaction of tert-leucine and 2,2-dimethylpentan-3-one with dimethyl fumarate with subsequent conversion of the resulting strained pyrrolidine into 1-pyrroline-1-oxide and addition of EtLi. The nitroxide has demonstrated unexpectedly fast reduction with ascorbate, the rate constant k2 = (2.0 ± 0.1) × 10−3 M−1s−1. This effect was explained by destabilization of the planar nitroxide moiety due to repulsion with the two neighboring tert-butyl groups cis to each other. Full article
(This article belongs to the Special Issue Recent Advances in Domino Reactions)
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Review

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27 pages, 16304 KiB  
Review
Recent Advances in the Domino Annulation Reaction of Quinone Imines
by Zhen-Hua Wang, Xiao-Hui Fu, Qun Li, Yong You, Lei Yang, Jian-Qiang Zhao, Yan-Ping Zhang and Wei-Cheng Yuan
Molecules 2024, 29(11), 2481; https://doi.org/10.3390/molecules29112481 - 24 May 2024
Viewed by 1209
Abstract
Quinone imines are important derivatives of quinones with a wide range of applications in organic synthesis and the pharmaceutical industry. The attack of nucleophilic reagents on quinone imines tends to lead to aromatization of the quinone skeleton, resulting in both the high reactivity [...] Read more.
Quinone imines are important derivatives of quinones with a wide range of applications in organic synthesis and the pharmaceutical industry. The attack of nucleophilic reagents on quinone imines tends to lead to aromatization of the quinone skeleton, resulting in both the high reactivity and the unique reactivity of quinone imines. The extreme value of quinone imines in the construction of nitrogen- or oxygen-containing heterocycles has attracted widespread attention, and remarkable advances have been reported recently. This review provides an overview of the application of quinone imines in the synthesis of cyclic compounds via the domino annulation reaction. Full article
(This article belongs to the Special Issue Recent Advances in Domino Reactions)
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