Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids
The reductive cyclization of arenetellurols carrying α,β-unsaturated amide functionalities in the ortho position was investigated. Conceptually, such compounds can form 1,3-tellurazoles without the involvement of the unsaturation in the ring closure, they can form 1,4-tellurazinone derivatives, or t...
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| Format: | Article |
| Language: | English |
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Wiley
2021-01-01
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| Series: | Heteroatom Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2021/7140222 |
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| author | Jayna A. Patel Aundrea M. Lee Donna V. Franklin Frank R. Fronczek Thomas Junk |
| author_facet | Jayna A. Patel Aundrea M. Lee Donna V. Franklin Frank R. Fronczek Thomas Junk |
| author_sort | Jayna A. Patel |
| collection | DOAJ |
| description | The reductive cyclization of arenetellurols carrying α,β-unsaturated amide functionalities in the ortho position was investigated. Conceptually, such compounds can form 1,3-tellurazoles without the involvement of the unsaturation in the ring closure, they can form 1,4-tellurazinone derivatives, or they can undergo ring closure to 1,5-tellurazepinones. Amides derived from acrylic and methacrylic acid generated 1,5-tellurazepinones while 2-cinnamylamidobenzenetellurol cyclized to a 1,3-tellurazole derivative. In contrast, the reaction of acetylenedicarboxylic acid and its derivatives with 2-aminoarenetellurols generated 1,4-tellurazepinones, including a derivative of novel tricyclic naphtho [1, 4]tellurazinone. A comparison with analogous reactions of sulfur congeners indicates that their chemistry is a good predictor for the products obtained from 2-aminoarenetellurols. Selected compounds were characterized by X-ray crystallography. The present work offers access to previously unexplored organotellurium heterocycles. |
| format | Article |
| id | doaj-art-7db50679eb97495bad7a2236743b7bed |
| institution | Kabale University |
| issn | 1098-1071 |
| language | English |
| publishDate | 2021-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Heteroatom Chemistry |
| spelling | doaj-art-7db50679eb97495bad7a2236743b7bed2025-02-03T01:31:26ZengWileyHeteroatom Chemistry1098-10712021-01-01202110.1155/2021/7140222Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic AcidsJayna A. Patel0Aundrea M. Lee1Donna V. Franklin2Frank R. Fronczek3Thomas Junk4Department of ChemistryDepartment of ChemistryDepartment of ChemistryDepartment of ChemistryDepartment of ChemistryThe reductive cyclization of arenetellurols carrying α,β-unsaturated amide functionalities in the ortho position was investigated. Conceptually, such compounds can form 1,3-tellurazoles without the involvement of the unsaturation in the ring closure, they can form 1,4-tellurazinone derivatives, or they can undergo ring closure to 1,5-tellurazepinones. Amides derived from acrylic and methacrylic acid generated 1,5-tellurazepinones while 2-cinnamylamidobenzenetellurol cyclized to a 1,3-tellurazole derivative. In contrast, the reaction of acetylenedicarboxylic acid and its derivatives with 2-aminoarenetellurols generated 1,4-tellurazepinones, including a derivative of novel tricyclic naphtho [1, 4]tellurazinone. A comparison with analogous reactions of sulfur congeners indicates that their chemistry is a good predictor for the products obtained from 2-aminoarenetellurols. Selected compounds were characterized by X-ray crystallography. The present work offers access to previously unexplored organotellurium heterocycles.http://dx.doi.org/10.1155/2021/7140222 |
| spellingShingle | Jayna A. Patel Aundrea M. Lee Donna V. Franklin Frank R. Fronczek Thomas Junk Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids Heteroatom Chemistry |
| title | Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids |
| title_full | Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids |
| title_fullStr | Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids |
| title_full_unstemmed | Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids |
| title_short | Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids |
| title_sort | cyclization reactions involving 2 aminoarenetellurols and derivatives of α β unsaturated carboxylic acids |
| url | http://dx.doi.org/10.1155/2021/7140222 |
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