Two independent and consecutive Michael addition of 1,3-dimethylbarbituric acid to (2,6-diarylidene)cyclohexanone: Flying-bird-shaped 2D-polymeric structure

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Pesyan N. N., Mousavi S., ŞAHİN E.

HETEROCYCLIC COMMUNICATIONS, cilt.28, sa.1, ss.44-50, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 28 Sayı: 1
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1515/hc-2022-0009
  • Dergi Adı: HETEROCYCLIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Directory of Open Access Journals
  • Sayfa Sayıları: ss.44-50
  • Anahtar Kelimeler: crossed-aldol condensation, consecutive Michael addition, 1, 3-dimethylbarbituric acid, conformation, bifurcated H-bond, CROSS-ALDOL CONDENSATION, CLAISEN-SCHMIDT CONDENSATION, CATALYST-FREE SYNTHESIS, DOUBLE AZA-MICHAEL, FACILE SYNTHESIS, EFFICIENT SYNTHESIS, AROMATIC-ALDEHYDES, IONIC LIQUID, CYCLOALKANONES, CONVENIENT
  • Atatürk Üniversitesi Adresli: Evet

Özet

Two independent and consecutive intermolecular Michael addition of 1,3-dimethylbarbituric acid to 2,6-diarylidenecyclohexanone as an alpha,beta-unsaturated ketone leads to synthesis of a new type of meso form 5,5 '-((2-oxocyclohexane-1,3-diyl)bis(arylmethylene))bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) in good yield. These compounds showed a 2D-polymeric structure via intermolecular H-bonds. Structure elucidation is carried out by H-1 NMR, C-13 NMR, FT-IR, and X-ray diffraction analyses. A plausible reaction mechanism is discussed.