Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides
Based on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
De Gruyter
2019-11-01
|
| Series: | Heterocyclic Communications |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/hc-2019-0020 |
| _version_ | 1819121975427072000 |
|---|---|
| author | Zadorozhnii Pavlo V. Pokotylo Ihor O. Kiselev Vadym V. Kharchenko Aleksandr V. Okhtina Oxana V. |
| author_facet | Zadorozhnii Pavlo V. Pokotylo Ihor O. Kiselev Vadym V. Kharchenko Aleksandr V. Okhtina Oxana V. |
| author_sort | Zadorozhnii Pavlo V. |
| collection | DOAJ |
| description | Based on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides. The reaction was carried out in boiling glacial acetic acid for 1-1.5 hours. The cyclization products were obtained in 42-62% yields and easily isolated from the reaction mixture. The structure of all synthesized compounds was confirmed by complex spectral studies. |
| first_indexed | 2024-12-22T06:45:06Z |
| format | Article |
| id | doaj.art-82568967560d40e9bc2f96f3c3595d8e |
| institution | Directory Open Access Journal |
| issn | 2191-0197 |
| language | English |
| last_indexed | 2024-12-22T06:45:06Z |
| publishDate | 2019-11-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Heterocyclic Communications |
| spelling | doaj.art-82568967560d40e9bc2f96f3c3595d8e2022-12-21T18:35:19ZengDe GruyterHeterocyclic Communications2191-01972019-11-0125113013710.1515/hc-2019-0020Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamidesZadorozhnii Pavlo V.0Pokotylo Ihor O.1Kiselev Vadym V.2Kharchenko Aleksandr V.3Okhtina Oxana V.4Department of Organic Substances and Pharmaceutical Preparations, Ukrainian State University of Chemical Technology, Gagarin Ave., 8, Dnipro 49005, UkraineDepartment of Organic Substances and Pharmaceutical Preparations, Ukrainian State University of Chemical Technology, Gagarin Ave., 8, Dnipro 49005, UkraineDepartment of Organic Substances and Pharmaceutical Preparations, Ukrainian State University of Chemical Technology, Gagarin Ave., 8, Dnipro 49005, UkraineDepartment of Organic Substances and Pharmaceutical Preparations, Ukrainian State University of Chemical Technology, Gagarin Ave., 8, Dnipro 49005, UkraineDepartment of Organic Substances and Pharmaceutical Preparations, Ukrainian State University of Chemical Technology, Gagarin Ave., 8, Dnipro 49005, UkraineBased on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides. The reaction was carried out in boiling glacial acetic acid for 1-1.5 hours. The cyclization products were obtained in 42-62% yields and easily isolated from the reaction mixture. The structure of all synthesized compounds was confirmed by complex spectral studies.https://doi.org/10.1515/hc-2019-0020dehydrosulfurization[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazolethioureasn-amidoalkylated |
| spellingShingle | Zadorozhnii Pavlo V. Pokotylo Ihor O. Kiselev Vadym V. Kharchenko Aleksandr V. Okhtina Oxana V. Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides Heterocyclic Communications dehydrosulfurization [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole thioureas n-amidoalkylated |
| title | Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides |
| title_full | Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides |
| title_fullStr | Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides |
| title_full_unstemmed | Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides |
| title_short | Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides |
| title_sort | synthesis and spectral characteristics of n 1 1 2 4 triazolo 3 4 b 1 3 4 thiadiazol 6 ylamino 2 2 2 trichloroethyl carboxamides |
| topic | dehydrosulfurization [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole thioureas n-amidoalkylated |
| url | https://doi.org/10.1515/hc-2019-0020 |
| work_keys_str_mv | AT zadorozhniipavlov synthesisandspectralcharacteristicsofn1124triazolo34b134thiadiazol6ylamino222trichloroethylcarboxamides AT pokotyloihoro synthesisandspectralcharacteristicsofn1124triazolo34b134thiadiazol6ylamino222trichloroethylcarboxamides AT kiselevvadymv synthesisandspectralcharacteristicsofn1124triazolo34b134thiadiazol6ylamino222trichloroethylcarboxamides AT kharchenkoaleksandrv synthesisandspectralcharacteristicsofn1124triazolo34b134thiadiazol6ylamino222trichloroethylcarboxamides AT okhtinaoxanav synthesisandspectralcharacteristicsofn1124triazolo34b134thiadiazol6ylamino222trichloroethylcarboxamides |