Article
2022
·
1 citations
Two independent and consecutive Michael addition of 1,3-dimethylbarbituric acid to (2,6-diarylidene)cyclohexanone: Flying-bird-shaped 2D-polymeric structure
Abstract
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.
Keywords
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
WoS Categories
Chemistry, Organic
Sustainable Development Goals
Citation
- Journal
- HETEROCYCLIC COMMUNICATIONS
- Year
- 2022
- Volume
- 28
- Issue
- 1
- Pages
- 44-50
- ISSN
- 0793-0283
- eISSN
- 2191-0197
- DOI
- 10.1515/hc-2022-0009
- WoS UID
- WOS:000787908300001