LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazoles
A two-step, one-pot synthesis of 3-substituted 1<i>H</i>-dibenzo[<i>e</i>,<i>g</i>]indazoles in good to high yields via a LiO<i><sup>t</sup></i>Bu-promoted intramolecular 1,3-dipolar cyclization of 2′-alkynyl-biaryl-2-aldehyde <i>N<...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/24/8061 |
| _version_ | 1827573986864660480 |
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| author | Jiaying Lv Ruimao Hua |
| author_facet | Jiaying Lv Ruimao Hua |
| author_sort | Jiaying Lv |
| collection | DOAJ |
| description | A two-step, one-pot synthesis of 3-substituted 1<i>H</i>-dibenzo[<i>e</i>,<i>g</i>]indazoles in good to high yields via a LiO<i><sup>t</sup></i>Bu-promoted intramolecular 1,3-dipolar cyclization of 2′-alkynyl-biaryl-2-aldehyde <i>N</i>-tosylhydrazones was developed. The <i>N</i>-Ts-hydrazones used were prepared in situ via the reactions of 2′-alkynyl-biaryl-2-aldehydes and TsNHNH<sub>2</sub> <i>(p</i>-methylbenzenesulfonohydrazide). Two types of signals related to the hydrogen bonds, forming in several products, were observed in the <sup>1</sup>H NMR spectra recorded in DMSO-<i>d</i><sub>6</sub>, assigned to N-H bonds in their dimeric species of product and tautomer. |
| first_indexed | 2024-03-08T20:30:00Z |
| format | Article |
| id | doaj.art-738e1b26158f45d8b2c13a3b33764bc0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T20:30:00Z |
| publishDate | 2023-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-738e1b26158f45d8b2c13a3b33764bc02023-12-22T14:27:38ZengMDPI AGMolecules1420-30492023-12-012824806110.3390/molecules28248061LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazolesJiaying Lv0Ruimao Hua1Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, ChinaKey Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, ChinaA two-step, one-pot synthesis of 3-substituted 1<i>H</i>-dibenzo[<i>e</i>,<i>g</i>]indazoles in good to high yields via a LiO<i><sup>t</sup></i>Bu-promoted intramolecular 1,3-dipolar cyclization of 2′-alkynyl-biaryl-2-aldehyde <i>N</i>-tosylhydrazones was developed. The <i>N</i>-Ts-hydrazones used were prepared in situ via the reactions of 2′-alkynyl-biaryl-2-aldehydes and TsNHNH<sub>2</sub> <i>(p</i>-methylbenzenesulfonohydrazide). Two types of signals related to the hydrogen bonds, forming in several products, were observed in the <sup>1</sup>H NMR spectra recorded in DMSO-<i>d</i><sub>6</sub>, assigned to N-H bonds in their dimeric species of product and tautomer.https://www.mdpi.com/1420-3049/28/24/8061<i>N</i>-tosylhydrazones1<i>H</i>-dibenzo[<i>e</i>,<i>g</i>]indazolesintramolecular cycloadditionlithium <i>tert</i>-butoxidehydrogen bonds |
| spellingShingle | Jiaying Lv Ruimao Hua LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazoles Molecules <i>N</i>-tosylhydrazones 1<i>H</i>-dibenzo[<i>e</i>,<i>g</i>]indazoles intramolecular cycloaddition lithium <i>tert</i>-butoxide hydrogen bonds |
| title | LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazoles |
| title_full | LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazoles |
| title_fullStr | LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazoles |
| title_full_unstemmed | LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazoles |
| title_short | LiO<i><sup>t</sup></i>Bu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde <i>N</i>-Tosylhydrazones Approach to 3-Substituted 1<i>H</i>-Dibenzo[<i>e</i>,<i>g</i>]indazoles |
| title_sort | lio i sup t sup i bu promoted intramolecular 1 3 dipolar cycloaddition of the 2 alkynyl biaryl 2 aldehyde i n i tosylhydrazones approach to 3 substituted 1 i h i dibenzo i e i i g i indazoles |
| topic | <i>N</i>-tosylhydrazones 1<i>H</i>-dibenzo[<i>e</i>,<i>g</i>]indazoles intramolecular cycloaddition lithium <i>tert</i>-butoxide hydrogen bonds |
| url | https://www.mdpi.com/1420-3049/28/24/8061 |
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