Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile
A general methodology to access valuable 4-(phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines was developed by the reaction of 2-azidobenzaldehyde with phenylchalcogenylacetonitriles (sulfur and selenium) in the presence of potassium carbonate (20 mol%) as a catalyst. The reactions wer...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/5036 |
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| author | Loana I. Monzon Nicole C. M. Rocha Gabriela T. Quadros Pâmela P. P. Nunes Roberta Cargnelutti Raquel G. Jacob Eder J. Lenardão Gelson Perin Daniela Hartwig |
| author_facet | Loana I. Monzon Nicole C. M. Rocha Gabriela T. Quadros Pâmela P. P. Nunes Roberta Cargnelutti Raquel G. Jacob Eder J. Lenardão Gelson Perin Daniela Hartwig |
| author_sort | Loana I. Monzon |
| collection | DOAJ |
| description | A general methodology to access valuable 4-(phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines was developed by the reaction of 2-azidobenzaldehyde with phenylchalcogenylacetonitriles (sulfur and selenium) in the presence of potassium carbonate (20 mol%) as a catalyst. The reactions were conducted using a mixture of dimethylsulfoxide and water (7:3) as solvent at 80 °C for 4 h. This new methodology presents a good functional group tolerance to electron-deficient and electron-rich substituents, affording a total of twelve different 4-(phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines selectively in moderate to excellent yields. The structure of the synthesized 4-(phenylselanyl)tetrazolo[1,5-<i>a</i>]quinoline was confirmed by X-ray analysis. |
| first_indexed | 2024-03-11T01:33:51Z |
| format | Article |
| id | doaj.art-0d7f125de0304cf7988c0d4e3185f2e2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:33:51Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0d7f125de0304cf7988c0d4e3185f2e22023-11-18T17:07:15ZengMDPI AGMolecules1420-30492023-06-012813503610.3390/molecules28135036Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with PhenylchalcogenylacetonitrileLoana I. Monzon0Nicole C. M. Rocha1Gabriela T. Quadros2Pâmela P. P. Nunes3Roberta Cargnelutti4Raquel G. Jacob5Eder J. Lenardão6Gelson Perin7Daniela Hartwig8Laboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLaboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLaboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLaboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilDepartamento de Química, Universidade Federal de Santa Maria—UFSM, Av. Roraima, Building 18, Santa Maria 97105-900, RS, BrazilLaboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLaboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLaboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilLaboratório de Síntese Orgânica Limpa-LaSOL-CCQFA, Universidade Federal de Pelotas—UFPel, P.O. Box 354, Pelotas 96010-900, RS, BrazilA general methodology to access valuable 4-(phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines was developed by the reaction of 2-azidobenzaldehyde with phenylchalcogenylacetonitriles (sulfur and selenium) in the presence of potassium carbonate (20 mol%) as a catalyst. The reactions were conducted using a mixture of dimethylsulfoxide and water (7:3) as solvent at 80 °C for 4 h. This new methodology presents a good functional group tolerance to electron-deficient and electron-rich substituents, affording a total of twelve different 4-(phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines selectively in moderate to excellent yields. The structure of the synthesized 4-(phenylselanyl)tetrazolo[1,5-<i>a</i>]quinoline was confirmed by X-ray analysis.https://www.mdpi.com/1420-3049/28/13/5036organochalcogentetrazolequinolinescyclizationheterocycles |
| spellingShingle | Loana I. Monzon Nicole C. M. Rocha Gabriela T. Quadros Pâmela P. P. Nunes Roberta Cargnelutti Raquel G. Jacob Eder J. Lenardão Gelson Perin Daniela Hartwig Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile Molecules organochalcogen tetrazolequinolines cyclization heterocycles |
| title | Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile |
| title_full | Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile |
| title_fullStr | Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile |
| title_full_unstemmed | Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile |
| title_short | Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-<i>a</i>]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile |
| title_sort | synthesis of 4 phenylchalcogenyl tetrazolo 1 5 i a i quinolines by bicyclization of 2 azidobenzaldehydes with phenylchalcogenylacetonitrile |
| topic | organochalcogen tetrazolequinolines cyclization heterocycles |
| url | https://www.mdpi.com/1420-3049/28/13/5036 |
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