A decade update on the application of β-oxodithioesters in heterocyclic synthesis
The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioeste...
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| Published in | Organic & biomolecular chemistry Vol. 21; no. 34; pp. 686 - 6829 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
30.08.2023
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1477-0520 1477-0539 1477-0539 |
| DOI | 10.1039/d3ob00601h |
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| Abstract | The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers (
i.e.
, α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles (
e.g.
, thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks.
A decade update on the application of β-oxodithioesters in the construction of sulfur-containing heterocycles, non-sulfur heterocycles, and other open-chain frameworks is presented. |
|---|---|
| AbstractList | The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers (
i.e.
, α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles (
e.g.
, thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks.
A decade update on the application of β-oxodithioesters in the construction of sulfur-containing heterocycles, non-sulfur heterocycles, and other open-chain frameworks is presented. The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers (i.e., α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles (e.g., thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks. The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers (i.e., α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles (e.g., thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks.The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers (i.e., α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles (e.g., thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks. The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers ( , α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles ( , thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks. The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers ( i.e. , α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles ( e.g. , thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks. |
| Author | Dong, Zhi-Bing Cheng, Bin Dou, Qian Wang, Taimin Gong, Zhiying |
| AuthorAffiliation | Lanzhou Institute of Chemical Physics Chinese Academy of Sciences Key Laboratory of Science and Technology on Wear and Protection of Materials School of Chemistry and Environmental Engineering Wuhan Institute of Technology Shenzhen Polytechnic Institute of Marine Biomedicine |
| AuthorAffiliation_xml | – sequence: 0 name: Shenzhen Polytechnic – sequence: 0 name: Key Laboratory of Science and Technology on Wear and Protection of Materials – sequence: 0 name: Chinese Academy of Sciences – sequence: 0 name: Institute of Marine Biomedicine – sequence: 0 name: Lanzhou Institute of Chemical Physics – sequence: 0 name: School of Chemistry and Environmental Engineering – sequence: 0 name: Wuhan Institute of Technology |
| Author_xml | – sequence: 1 givenname: Zhi-Bing surname: Dong fullname: Dong, Zhi-Bing – sequence: 2 givenname: Zhiying surname: Gong fullname: Gong, Zhiying – sequence: 3 givenname: Qian surname: Dou fullname: Dou, Qian – sequence: 4 givenname: Bin surname: Cheng fullname: Cheng, Bin – sequence: 5 givenname: Taimin surname: Wang fullname: Wang, Taimin |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37555699$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_rechem_2024_101977 crossref_primary_10_1039_D5OB00022J |
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| Snippet | The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted... |
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| SubjectTerms | Chemical synthesis Heterocyclic compounds Nitrogen Organic chemistry Organic compounds Pyridines Quinolines Reagents Sulfur Thiazoles Thiophenes |
| Title | A decade update on the application of β-oxodithioesters in heterocyclic synthesis |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/37555699 https://www.proquest.com/docview/2858604747 https://www.proquest.com/docview/2848229678 |
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