Synthesis of Biginelli dihydropyrimidinone derivatives with various substituents on aluminium-planted mesoporous silica catalyst.
Biginelli reactions were well catalyzed on mesoporous silica MCM-41 (M41) whose activity was much greater than that of amorphous silica. Octane was the most suitable among 6 kinds of solvents examined. The addition of metal ions on M41 enhanced the catalytic activity in the order Al > Ti > Fe = In. Al-planted M41s with Si/Al ratios of 45-35 showed the highest catalytic activity and could be used repeatedly though a small loss of the activity was observed. The catalysis could widely be applied to obtain various substituted dihydropyrimidinones (DHPMs) with high yields, some of which were very difficult to prepare until now. In addition, Biginelli reactions were combined with formyl C-H insertion reactions of diazoester on mesoporous silica; that is, a tandem one-pot four-component DHPM synthesis was attempted. Acetaldehyde, ethyl diazoacetate, p-tolualdehyde, and urea could be condensed and the corresponding DHPM derivative was obtained with 50% yield on Al-planted M41.
Murata
Hiroaki
H
Chemical Resources Laboratory, Tokyo Institute of Technology, 4259-R1-5 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan.
Ishitani
Haruro
H
Iwamoto
Masakazu
M
D000535:Aluminum / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry*; D012997:Solvents
C509968:MCM-41; D011744:Pyrimidinones; D012997:Solvents; D012822:Silicon Dioxide; D000535:Aluminum