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

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

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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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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