IJOC  Vol.1 No.4 , December 2011
Dimethylformamide Dimethyl Acetal (DMFDMA) in Heterocyclic Synthesis: Synthesis of Polysubstituted Pyridines, Pyrimidines, Pyridazine and Their Fused Derivatives
Abstract: Reaction of N,N’-dimethylformamide dimethyl acetal (DMFDMA) with malononitrile dimer 8 (1:1) mole afforded 9 while, this reaction when carried out in (2:1) mole to give amidine 11 which can be used for the preparation of pyrimidine 13, amidine 14 and pyridine 19 when reacted with 4-nitroaniline, 4-methylaniline and alkoxide respectively. Malononitrile dimer reacted with diazonium chloride to give pyridazine 21, which can be reacted with DMFDMA, AcOH/HCl and cyanoacetamide to give pyridazine 22, 23 and pyrido[4,3-c] pyridazine 24 respectively. The latter reacted with DMFDMA to afford tricyclic compound 25.
Cite this paper: nullF. Abu-Shanab, S. Mousa, E. Eshak, A. Sayed and A. Al-Harrasi, "Dimethylformamide Dimethyl Acetal (DMFDMA) in Heterocyclic Synthesis: Synthesis of Polysubstituted Pyridines, Pyrimidines, Pyridazine and Their Fused Derivatives," International Journal of Organic Chemistry, Vol. 1 No. 4, 2011, pp. 207-214. doi: 10.4236/ijoc.2011.14030.

[1]   V. G. Granik, A. M. Zhidkova and R. G. Glushkov, “Advances in the Chemistry of the Acetals of Acid Amides and Lactams,” Russian Chemical Reviews, Vol. 46, No. 4, 1977, pp. 361-366. doi:10.1070/RC1977v046n04ABEH002137

[2]   R. F. Abdulla and R. S. Brinkmeyer, “The Chemistry of Formamide Acetals,” Tetrahedron, Vol. 35, No. 14, 1979, pp. 1675-1735. doi:10.1016/0040-4020(79)88001-1

[3]   P. L. Anelli, M. Brocchetta, D. Palano and M. Visigalli, “Mild Conversion of Primary Carboxamides into Carboxylic Esters,” Tetrahedron Letters, Vol. 38, No. 13, 1997, pp. 2367-2368. doi:10.1016/S0040-4039(97)00350-X

[4]   M. Malesic, A. Krbavcic, A. Golobic, L. Golic and B. Stanovenik, “The Synthesis and Transformation of Ethyl 2-(2-Acetyl-2-benzoyl-1-ethenyl)amino-3-dimethylaminopropenoate. A New Synthesis of 2,3,4-Trisubstituted Pyrroles,” Journal of Heterocyclic Chemistry, Vol. 34, No. 6, 1997, pp. 1757-1762. doi:10.1002/jhet.5570340619

[5]   F. A. Abu-Shanab, A. D. Redhouse, J. R. Thompson and B. J. Wakefield, “Synthesis of 2,3,5,6-Tetrasubstituted Pyridines from Enamines Derived from N,N-Dimethyl- formamide Dimethyl Acetal,” Synthesis, Vol. 5, 1995, pp. 557-560. doi:10.1055/s-1995-3954

[6]   F. A. Abu-Shanab, F. M. Aly and B. J. Wakefield, “Synthesis of Substituted Nicotinamides from Enamines Derived from N,N-Dimethylformamide Dimethyl Acetal,” Synthesis, Vol. 8, 1995, pp. 923-925. doi:10.1055/s-1995-4039

[7]   F. A. Abu-Shanab, A. M. Hessen and S. A. S. Mousa, “Dimethylformamide Dimethyl Acetal in Heterocyclic Synthesis: Synthesis of Polyfunctionally Substituted Pyridine Derivatives as Precursors to Bicycles and Polycycles,” Journal of Heterocyclic Chemistry, Vol. 44, No. 4, 2007, pp. 787-791. doi:10.1002/jhet.5570440406

[8]   F. A. Abu-Shanab, M. H. Elnagdi, F. M. Aly and B. J. Wakefield, Journal of the Chemical Society, Perkin Tran- sactions 1, Vol. 1, 1994, pp. 1449-1452.

[9]   F. A. Abu-Shanab, S. A. S. Mousa, et al., “Dimethylformamide Dimethyl acetal as a Building Block in Heterocyclic Synthesis,” Journal of Heterocyclic Chemistry, Vol. 46, No. 5, 2009, pp. 801-827. doi:10.1002/jhet.69

[10]   F. A. Abu-Shanab, A. El-Harrasi and S. A. S. Mousa, “Synthesis of 1,4-Diaryl-piperazine-2,5-diones: New Behavior of N,N-Dimethylformamide Dimethyl Acetal (DMF DMA),” Synthetic Communications, Vol. 38, No. 3, 2008, pp. 376-382. doi:10.1080/00397910701767098

[11]   R. A. Carboni, D. D. Conffman and E. G. Howard, “Cyanocarbon Chemistry. XI.1 Malononitrile Dimer,” Journal of the American Chemical Society, Vol. 80, No. 11, 1958, pp. 2838-2840.

[12]   F. A. Abu-Shanab, Y. M. Elkholy and M. H. Elnagdi, “Enaminones as Building Blocks in Organic Synthesis: Synthesis of New Polyfunctional Pyridines, Condensed Pyridines, and Penta Substituted Benzene,” Synthetic Communications, Vol. 32, No. 22, 2002, pp. 3493-3502.