A1 Journal article (refereed)
Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Derivatives : X-ray Single Crystal Structure and Hirshfeld Analyses (2022)
Boraei, A. T. A., Haukka, M., Sopaih, M., Al-Majid, A. M., Soliman, S. M., Barakat, A., & Sarhan, A. A. M. (2022). Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Derivatives : X-ray Single Crystal Structure and Hirshfeld Analyses. Crystals, 12(2), Article 262. https://doi.org/10.3390/cryst12020262
JYU authors or editors
Publication details
All authors or editors: Boraei, Ahmed T. A.; Haukka, Matti; Sopaih, Manar; Al-Majid, Abdullah Mohammed; Soliman, Saied M.; Barakat, Assem; Sarhan, Ahmed A. M.
Journal or series: Crystals
eISSN: 2073-4352
Publication year: 2022
Publication date: 15/02/2022
Volume: 12
Issue number: 2
Article number: 262
Publisher: MDPI AG
Publication country: Switzerland
Publication language: English
DOI: https://doi.org/10.3390/cryst12020262
Publication open access: Openly available
Publication channel open access: Open Access channel
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/80503
Abstract
A straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one was subjected to aza-Michael addition and N-alkylation on reaction with a set of alkylating agents in the presence of K2CO3. Hydrazinolysis of 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one ester to hydrazide and conversion of hydrazide to thiosemicarbazide were successful. X-Ray single crystals analysis and 1H, 13C NMR were used for unambiguous structure confirmation. The O…H, N…H, C…N and C…C in 2, and the N…H, C…N, C…C, C…O and H…H interactions in 6 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.
Keywords: heterocyclic compounds; aromatic compounds; chemical synthesis
Free keywords: fluoranthenes; polycyclic aromatic heterocycles; aza-Michael addition; N-alkylation; Hirshfeld Analyses
Contributing organizations
Ministry reporting: Yes
Reporting Year: 2022
JUFO rating: 1