5,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione
1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this commun...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-05-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/2/M1649 |
| _version_ | 1797593322616782848 |
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| author | Timofey N. Chmovzh Karim S. Gaisin Oleg A. Rakitin |
| author_facet | Timofey N. Chmovzh Karim S. Gaisin Oleg A. Rakitin |
| author_sort | Timofey N. Chmovzh |
| collection | DOAJ |
| description | 1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for the synthesis of 4,7-dihalo-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazines, is formed via the cyclization of 1,2,5-oxadiazole-3,4-dicarbohydrazide in hydrochloric acid. The structure of the newly synthesized compound was established by means of elemental analysis; high-resolution mass spectrometry; <sup>1</sup>H and <sup>13</sup>C NMR; IR spectroscopy, and mass spectrometry. |
| first_indexed | 2024-03-11T02:07:27Z |
| format | Article |
| id | doaj.art-8a4359619dd6491f896c2f180975d184 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T02:07:27Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-8a4359619dd6491f896c2f180975d1842023-11-18T11:47:03ZengMDPI AGMolbank1422-85992023-05-0120232M164910.3390/M16495,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dioneTimofey N. Chmovzh0Karim S. Gaisin1Oleg A. Rakitin2N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, Moscow 119991, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, Moscow 119991, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, Moscow 119991, Russia1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for the synthesis of 4,7-dihalo-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazines, is formed via the cyclization of 1,2,5-oxadiazole-3,4-dicarbohydrazide in hydrochloric acid. The structure of the newly synthesized compound was established by means of elemental analysis; high-resolution mass spectrometry; <sup>1</sup>H and <sup>13</sup>C NMR; IR spectroscopy, and mass spectrometry.https://www.mdpi.com/1422-8599/2023/2/M1649[1,2,5]oxadiazolo[3,4-d]pyridazinesring closure5,6-dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| spellingShingle | Timofey N. Chmovzh Karim S. Gaisin Oleg A. Rakitin 5,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione Molbank [1,2,5]oxadiazolo[3,4-d]pyridazines ring closure 5,6-dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| title | 5,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| title_full | 5,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| title_fullStr | 5,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| title_full_unstemmed | 5,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| title_short | 5,6-Dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| title_sort | 5 6 dihydro 1 2 5 oxadiazolo 3 4 i d i pyridazine 4 7 dione |
| topic | [1,2,5]oxadiazolo[3,4-d]pyridazines ring closure 5,6-dihydro-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine-4,7-dione |
| url | https://www.mdpi.com/1422-8599/2023/2/M1649 |
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