Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS)
Triazolopyridines are a family of compounds that, owing to their biological activity, have many pharmaceutical applications. In this study, 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine and 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine were synthes...
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MDPI AG
2021-09-01
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| author | Said El-Kurdi Bassam Abu Thaher Kanan Wahedy Dieter Schollmeyer Levin Nopper Oliver Riester Hans-Peter Deigner |
| author_facet | Said El-Kurdi Bassam Abu Thaher Kanan Wahedy Dieter Schollmeyer Levin Nopper Oliver Riester Hans-Peter Deigner |
| author_sort | Said El-Kurdi |
| collection | DOAJ |
| description | Triazolopyridines are a family of compounds that, owing to their biological activity, have many pharmaceutical applications. In this study, 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine and 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine were synthesized by using the chlorinated agent NCS for hydrazones under very mild conditions. The characterization of these compounds was achieved by 1H NMR, <sup>13</sup>C NMR, FTIR, MS and X-ray diffraction. The compound 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine was crystallized in the monoclinic space group <i>P 2<sub>1</sub>/c</i> with <i>a</i> = 15.1413(12), <i>b</i> = 6.9179(4), <i>c</i> = 13.0938(8) Å, β = 105.102(6)°, <i>V</i> = 1324.16(16)Å<sup>3</sup>, <i>Z</i> = 4, and <i>R</i> = 0.0337. Also compound 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine was crystallized in the monoclinic space group <i>P 2<sub>1</sub>/c</i> with <i>a</i> = 14.3213(11), <i>b</i> = 6.9452(4) (4), <i>c</i> = 12.6860(8)Å, β = 100.265(6)°, <i>V</i> = 1241.62(14)Å<sup>3</sup>, <i>Z</i> = 4, and <i>R</i> = 0.0561. |
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| language | English |
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| spelling | doaj.art-a37e5c7761eb445d95f9f0254bbb8a932023-11-22T17:52:30ZengMDPI AGCrystals2073-43522021-09-011110115610.3390/cryst11101156Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS)Said El-Kurdi0Bassam Abu Thaher1Kanan Wahedy2Dieter Schollmeyer3Levin Nopper4Oliver Riester5Hans-Peter Deigner6Faculty of Science, Chemistry Department, Islamic University of Gaza, Gaza P.O. Box 108, PalestineFaculty of Science, Chemistry Department, Islamic University of Gaza, Gaza P.O. Box 108, PalestineFaculty of Pharmacy, Department of Pharmaceutical Chemistry, Alazhar University-Gaza, Gaza P.O. Box 1277, PalestineDepartment of Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128 Mainz, GermanyInstitute of Precision Medicine, Medical and Life Sciences Faculty, Furtwangen University, Jakob-Kienzle-Straße 17, 78054 Villingen-Schwenningen, GermanyInstitute of Precision Medicine, Medical and Life Sciences Faculty, Furtwangen University, Jakob-Kienzle-Straße 17, 78054 Villingen-Schwenningen, GermanyInstitute of Precision Medicine, Medical and Life Sciences Faculty, Furtwangen University, Jakob-Kienzle-Straße 17, 78054 Villingen-Schwenningen, GermanyTriazolopyridines are a family of compounds that, owing to their biological activity, have many pharmaceutical applications. In this study, 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine and 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine were synthesized by using the chlorinated agent NCS for hydrazones under very mild conditions. The characterization of these compounds was achieved by 1H NMR, <sup>13</sup>C NMR, FTIR, MS and X-ray diffraction. The compound 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine was crystallized in the monoclinic space group <i>P 2<sub>1</sub>/c</i> with <i>a</i> = 15.1413(12), <i>b</i> = 6.9179(4), <i>c</i> = 13.0938(8) Å, β = 105.102(6)°, <i>V</i> = 1324.16(16)Å<sup>3</sup>, <i>Z</i> = 4, and <i>R</i> = 0.0337. Also compound 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-<i>a</i>]pyridine was crystallized in the monoclinic space group <i>P 2<sub>1</sub>/c</i> with <i>a</i> = 14.3213(11), <i>b</i> = 6.9452(4) (4), <i>c</i> = 12.6860(8)Å, β = 100.265(6)°, <i>V</i> = 1241.62(14)Å<sup>3</sup>, <i>Z</i> = 4, and <i>R</i> = 0.0561.https://www.mdpi.com/2073-4352/11/10/11561,2,4-triazolo[4,3-<i>a</i>]pyridineNCSsynthesiscrystal structureH-bonding |
| spellingShingle | Said El-Kurdi Bassam Abu Thaher Kanan Wahedy Dieter Schollmeyer Levin Nopper Oliver Riester Hans-Peter Deigner Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS) Crystals 1,2,4-triazolo[4,3-<i>a</i>]pyridine NCS synthesis crystal structure H-bonding |
| title | Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS) |
| title_full | Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS) |
| title_fullStr | Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS) |
| title_full_unstemmed | Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS) |
| title_short | Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS) |
| title_sort | efficient synthesis and x ray structure of 1 2 4 triazolo 4 3 i a i pyridines via oxidative cyclization using n chlorosuccinimide ncs |
| topic | 1,2,4-triazolo[4,3-<i>a</i>]pyridine NCS synthesis crystal structure H-bonding |
| url | https://www.mdpi.com/2073-4352/11/10/1156 |
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