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