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Molecules 2010, 15(1), 58-67; doi:10.3390/molecules15010058

Enaminones in Heterocyclic Synthesis: A Novel Route to Tetrahydropyrimidines, Dihydropyridines, Triacylbenzenes and Naphthofurans under Microwave Irradiation

Department of Chemistry, Faculty of Science; Kuwait University, P.O. Box 5969 Safat, 13060, Kuwait
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Received: 27 October 2009 / Revised: 18 December 2009 / Accepted: 23 December 2009 / Published: 25 December 2009
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Abstract

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.
Keywords: enaminones; Biginelli's condensation; naphthofuran; zeolites; microwave irradiation with simultaneous cooling enaminones; Biginelli's condensation; naphthofuran; zeolites; microwave irradiation with simultaneous cooling
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MDPI and ACS Style

Al-Mousawi, S.M.; El-Apasery, M.A.; Elnagdi, M.H. Enaminones in Heterocyclic Synthesis: A Novel Route to Tetrahydropyrimidines, Dihydropyridines, Triacylbenzenes and Naphthofurans under Microwave Irradiation. Molecules 2010, 15, 58-67.

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