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Frontiers in Alkyne Chemistry
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Frontiers in Alkyne Chemistry

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

Deadline for manuscript submissions: closed (30 April 2024) | Viewed by 16697

Special Issue Editor

Prof. Dr. Ruimao Hua

E-Mail Website
Guest Editor
Department of Chemistry, Tsinghua University, Beijing 100084, China
Interests: organic synthesis; organic materials; catalytic transformation

Special Issue Information

Dear Colleagues,

The fields of organic chemistry and catalytic synthesis have gone through dramatic changes in recent decades, with an increasing emphasis on improvement of synthetic efficiency and reduction of waste to develop green chemistry. In this regard, alkynes, as one of the important classes of starting materials showing versatile applications, have recently experienced a tremendous growth in the development of atom-efficient organic reactions to synthesize functionalized alkenes, carbo- and heterocyclic compounds, which have been applied as synthetic intermediates, organic materials, drug candidates, and ligands. Because of the fast, advanced progress in atom-efficient organic synthesis starting from alkynes, a Special Issue on the subject of “Frontiers in Alkyne Chemistry” is planned to be published in Molecules.

The Special Issue on “Frontiers in Alkyne Chemistry” is seeking papers on advances in the synthesis and applications of alkynes. The objectives are to report new methods for the preparation of alkynes, the biological activity of alkynyl-containing compounds, and all the synthesis methodologies with alkynes, as well as organometallic chemistry with alkyne ligand. Communications, Articles, and Reviews are welcome.

Molecules in MDPI, as an open access journal, offers a great opportunity for your work to be viewed by larger numbers of readers and cited more frequently, as it is an excellent venue for organic chemists in academia and industry who wish to keep abreast with recent developments in the key fields of organic chemistry.

I look forward to having fruitful cooperation with you for this Special Issue publication.

Prof. Dr. Ruimao Hua
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

  • Alkyne annulation
  • Carbocycle synthesis
  • Heterocycle synthesis
  • Atom-economic reaction
  • Synthesis methodology

Published Papers (6 papers)

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Research

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9 pages, 627 KiB  
Article
Catalytic Enantioselective Cyclopropylalkynylation of Aldimines Generated In Situ from α-Amido Sulfones
by Alicia Monleón, Gonzalo Blay and José R. Pedro
Molecules 2022, 27(12), 3763; https://doi.org/10.3390/molecules27123763 - 11 Jun 2022
Cited by 1 | Viewed by 1214
Abstract
A convenient procedure of synthesis of N-carbamoyl-protected propargylic amines substituted with a cyclopropyl group from α-amido sulfones and cyclopropylacetylene is described. The reaction is catalyzed by a chiral BINOL-type zinc complex and provides the corresponding products in good yields and enantioselectivities. Full article
(This article belongs to the Special Issue Frontiers in Alkyne Chemistry)
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14 pages, 1057 KiB  
Article
Cu(I)/Pd(II)-Catalyzed Intramolecular Hydroamidation and C-H Dehydrogenative Coupling of ortho-Alkynyl-N-arylbenzamides for Access to Isoindolo[2,1-a]Indol-6-Ones
by Baoxin Tang and Ruimao Hua
Molecules 2022, 27(11), 3393; https://doi.org/10.3390/molecules27113393 - 25 May 2022
Cited by 2 | Viewed by 1398
Abstract
An efficient, atom-economic and one-pot synthesis of isoindolo[2,1-a]indol-6-ones via CuI/Pd(OAc)2-catalyzed intramolecular hydroamidation of alkynyl group, and C-H dehydrogenative coupling of ortho-alkynyl-N-arylbenzamides has been developed. This transformation occurs with the use of oxygen as the oxidant, and [...] Read more.
An efficient, atom-economic and one-pot synthesis of isoindolo[2,1-a]indol-6-ones via CuI/Pd(OAc)2-catalyzed intramolecular hydroamidation of alkynyl group, and C-H dehydrogenative coupling of ortho-alkynyl-N-arylbenzamides has been developed. This transformation occurs with the use of oxygen as the oxidant, and water is the only by-product. The reaction shows a high tolerance to a variety of functional groups, and affords isoindolo[2,1-a]indol-6-ones in good to high yields. Full article
(This article belongs to the Special Issue Frontiers in Alkyne Chemistry)
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27 pages, 5614 KiB  
Article
Synthesis of Anti-Inflammatory Spirostene-Pyrazole Conjugates by a Consecutive Multicomponent Reaction of Diosgenin with Oxalyl Chloride, Arylalkynes and Hydrazines or Hydrazones
by Maksim E. Mironov, Sergey A. Borisov, Tatyana V. Rybalova, Dmitry S. Baev, Tatyana G. Tolstikova and Elvira E. Shults
Molecules 2022, 27(1), 162; https://doi.org/10.3390/molecules27010162 - 28 Dec 2021
Viewed by 2230
Abstract
Steroid sapogenin diosgenin is of significant interest due to its biological activity and synthetic application. A consecutive one-pot reaction of diosgenin, oxalyl chloride, arylacetylenes, and phenylhydrazine give rise to steroidal 1,3,5-trisubstituted pyrazoles (isolated yield 46–60%) when the Stephens–Castro reaction and heterocyclization steps were [...] Read more.
Steroid sapogenin diosgenin is of significant interest due to its biological activity and synthetic application. A consecutive one-pot reaction of diosgenin, oxalyl chloride, arylacetylenes, and phenylhydrazine give rise to steroidal 1,3,5-trisubstituted pyrazoles (isolated yield 46–60%) when the Stephens–Castro reaction and heterocyclization steps were carried out by heating in benzene. When the cyclization step of alkyndione with phenylhydrazine was performed in 2-methoxyethanol at room temperature, steroidal α,β-alkynyl (E)- and (Z)-hydrazones were isolated along with 1,3,5-trisubstituted pyrazole and the isomeric 2,3,5-trisubstituted pyrazole. The consecutive reaction of diosgenin, oxalyl chloride, phenylacetylene and benzoic acid hydrazides efficiently forms steroidal 1-benzoyl-5-hydroxy-3-phenylpyrazolines. The structure of new compounds was unambiguously corroborated by comprehensive NMR spectroscopy, mass-spectrometry, and X-ray structure analyses. Performing the heterocyclization step of ynedione with hydrazine monohydrate in 2-methoxyethanol allowed the synthesis of 5-phenyl substituted steroidal pyrazole, which was found to exhibit high anti-inflammatory activity, comparable to that of diclofenac sodium, a commercial pain reliever. It was shown by molecular docking that the new derivatives are incorporated into the binding site of the protein Keap1 Kelch-domain by their alkynylhydrazone or pyrazole substituent with the formation of more non-covalent bonds and have higher affinity than the initial spirostene core. Full article
(This article belongs to the Special Issue Frontiers in Alkyne Chemistry)
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8 pages, 1806 KiB  
Article
Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source
by Hina Mehmood, Muhammad Asif Iqbal, Muhammad Naeem Ashiq and Ruimao Hua
Molecules 2021, 26(21), 6599; https://doi.org/10.3390/molecules26216599 - 31 Oct 2021
Cited by 2 | Viewed by 2052
Abstract
In the presence of Cs2CO3, the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine [...] Read more.
In the presence of Cs2CO3, the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine derivatives accompanies the outcome of 1,3-diaryl propenes, which are also useful intermediates in organic synthesis. Thus, pyridine ring results from a formal [2+2+1+1] cyclocondensation of three alkynes with benzamides, and one of the alkynes provides one carbon, whilst benzamides provide a nitrogen source only. A new transformation of alkynes as well as new utility of benzamide are found in this work. Full article
(This article belongs to the Special Issue Frontiers in Alkyne Chemistry)
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16 pages, 2395 KiB  
Article
Rhodium-Catalyzed Oxidative Annulation of 2- or 7-Arylindoles with Alkenes/Alkynes Using Molecular Oxygen as the Sole Oxidant Enabled by Quaternary Ammonium Salt
by Weihui Zhuang, Jiaqi Zhang, Yanping Zheng and Qiufeng Huang
Molecules 2021, 26(17), 5329; https://doi.org/10.3390/molecules26175329 - 2 Sep 2021
Cited by 4 | Viewed by 2065
Abstract
Developing an efficient catalytic system using molecular oxygen as the oxidant for rhodium-catalyzed cross-dehydrogenative coupling remains highly desirable. Herein, rhodium-catalyzed oxidative annulation of 2- or 7-phenyl-1H-indoles with alkenes or alkynes to assemble valuable 6H-isoindolo[2,1-a]indoles, pyrrolo[3,2,1-de]phenanthridines, [...] Read more.
Developing an efficient catalytic system using molecular oxygen as the oxidant for rhodium-catalyzed cross-dehydrogenative coupling remains highly desirable. Herein, rhodium-catalyzed oxidative annulation of 2- or 7-phenyl-1H-indoles with alkenes or alkynes to assemble valuable 6H-isoindolo[2,1-a]indoles, pyrrolo[3,2,1-de]phenanthridines, or indolo[2,1-a]isoquinolines using the atmospheric pressure of air as the sole oxidant enabled by quaternary ammonium salt has been accomplished. Mechanistic studies provided evidence for the fast intramolecular aza-Michael reaction and aerobic reoxidation of Rh(I)/Rh(III), facilitated by the addition of quaternary ammonium salt. Full article
(This article belongs to the Special Issue Frontiers in Alkyne Chemistry)
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Review

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27 pages, 6979 KiB  
Review
Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress
by Zhigeng Lin, Baoying Huang, Lufeng Ouyang and Liyao Zheng
Molecules 2022, 27(11), 3576; https://doi.org/10.3390/molecules27113576 - 2 Jun 2022
Cited by 5 | Viewed by 6847
Abstract
With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and [...] Read more.
With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area. Full article
(This article belongs to the Special Issue Frontiers in Alkyne Chemistry)
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