Journal
MOLECULES
Volume 15, Issue 1, Pages 58-67Publisher
MDPI
DOI: 10.3390/molecules15010058
Keywords
enaminones; Biginelli's condensation; naphthofuran; zeolites; microwave irradiation with simultaneous cooling
Funding
- Kuwait University, Research Administration [SC 05/06]
- SAF [GS 01/01, GS 03/01]
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Condensation of phthalimidoacetone (1) with DMFDMA (N, N-Dimethylformamide dimethyl acetal) has afforded enaminone 2. Refluxing 2 with equimolecular amounts of benzaldehyde and urea in acetic acid afforded a mixture of tetrahydropyrimidine 5 and the dihydropyridine 6. Compound 2 undergoes self-condensation on heating in acetic acid or under microwave irradiation in presence of acidic zeolite to give 1,3,5-triacylbenzene 9. Reacting enaminone 11a with naphthoquinone 15 afforded the naphthofuran 18. The possible formation of the aldehyde 19 was excluded based on an HMQC experiment, which revealed that the carbonyl carbon is not linked to any hydrogen.
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