Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses
A straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one was subjected t...
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| Format: | Article |
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MDPI AG
2022-02-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/12/2/262 |
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| author | Ahmed T. A. Boraei Matti Haukka Manar Sopaih Abdullah Mohammed Al-Majid Saied M. Soliman Assem Barakat Ahmed A. M. Sarhan |
| author_facet | Ahmed T. A. Boraei Matti Haukka Manar Sopaih Abdullah Mohammed Al-Majid Saied M. Soliman Assem Barakat Ahmed A. M. Sarhan |
| author_sort | Ahmed T. A. Boraei |
| collection | DOAJ |
| description | A straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one was subjected to <i>aza</i>-Michael addition and <i>N</i>-alkylation on reaction with a set of alkylating agents in the presence of K<sub>2</sub>CO<sub>3</sub>. Hydrazinolysis of 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one ester to hydrazide and conversion of hydrazide to thiosemicarbazide were successful. X-Ray single crystals analysis and <sup>1</sup>H, <sup>13</sup>C NMR were used for unambiguous structure confirmation. The O…H, N…H, C…N and C…C in <b>2</b>, and the N…H, C…N, C…C, C…O and H…H interactions in <b>6</b> are the most important in the molecular packing based on Hirshfled analysis. Moreover, the presence of short C…C and C…N contacts in both compounds revealed the presence of π–π stacking interactions. |
| first_indexed | 2024-03-09T22:14:17Z |
| format | Article |
| id | doaj.art-6085872c29794f99968522545bc02695 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-09T22:14:17Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-6085872c29794f99968522545bc026952023-11-23T19:25:38ZengMDPI AGCrystals2073-43522022-02-0112226210.3390/cryst12020262Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld AnalysesAhmed T. A. Boraei0Matti Haukka1Manar Sopaih2Abdullah Mohammed Al-Majid3Saied M. Soliman4Assem Barakat5Ahmed A. M. Sarhan6Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, FinlandChemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, EgyptDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaChemistry Department, Faculty of Science, Arish University, Al-Arish 45511, EgyptA straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one was subjected to <i>aza</i>-Michael addition and <i>N</i>-alkylation on reaction with a set of alkylating agents in the presence of K<sub>2</sub>CO<sub>3</sub>. Hydrazinolysis of 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one ester to hydrazide and conversion of hydrazide to thiosemicarbazide were successful. X-Ray single crystals analysis and <sup>1</sup>H, <sup>13</sup>C NMR were used for unambiguous structure confirmation. The O…H, N…H, C…N and C…C in <b>2</b>, and the N…H, C…N, C…C, C…O and H…H interactions in <b>6</b> are the most important in the molecular packing based on Hirshfled analysis. Moreover, the presence of short C…C and C…N contacts in both compounds revealed the presence of π–π stacking interactions.https://www.mdpi.com/2073-4352/12/2/262fluoranthenespolycyclic aromatic heterocycles<i>aza</i>-Michael addition<i>N</i>-alkylationHirshfeld Analyses |
| spellingShingle | Ahmed T. A. Boraei Matti Haukka Manar Sopaih Abdullah Mohammed Al-Majid Saied M. Soliman Assem Barakat Ahmed A. M. Sarhan Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses Crystals fluoranthenes polycyclic aromatic heterocycles <i>aza</i>-Michael addition <i>N</i>-alkylation Hirshfeld Analyses |
| title | Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses |
| title_full | Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses |
| title_fullStr | Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses |
| title_full_unstemmed | Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses |
| title_short | Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses |
| title_sort | straightforward one pot synthesis of new 4 phenyl 1 2 5 6 tetraazafluoranthen 3 2 i h i one derivatives x ray single crystal structure and hirshfeld analyses |
| topic | fluoranthenes polycyclic aromatic heterocycles <i>aza</i>-Michael addition <i>N</i>-alkylation Hirshfeld Analyses |
| url | https://www.mdpi.com/2073-4352/12/2/262 |
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