Synthesis of pyridine and pyrimidine derivatives by reaction of pyrylium salts with ureas, thioureas, and isothioureas

作者: �. A. Zvezdina , M. P. Zhdanova , G. N. Dorofeenko

DOI: 10.1007/BF00474088

关键词: PyrimidineUreaPyridineOrganic chemistryPerchlorateSemicarbazideAcetic anhydrideChemistry

摘要: 2,4,6-Triphenylpyrylium perchlorate is converted to 2,4,6-triphenylpyridine in reactions with urea and N-acetyl- N,N-dimethylureas, whereas it 1,2,4,6-tetraphenylpyridinium on reaction N,N′-diphenylurea. The of pyrylium perchlorates thiosemicarbazide semicarbazide leads 1-thiocarbamido- 1-carbamidopyridinium salts. latter reacts 2,4,6-triphenylpyrylium give 1-aminopyridinium salts, which were acylated acetic anhydride. Difficult-to-obtain 2-alkylthio-4,6-diarylpyrimidines synthesized 40–93% yields by the 2,4,6-triarylpyrylium salts S-alkylisothioureas.

参考文章(4)
A.T. Balaban, Reaction of pyrylium salts with nucleophiles—VII Tetrahedron. ,vol. 24, pp. 5059- 5065 ,(1968) , 10.1016/S0040-4020(01)88416-7
J.B. Bapat, R.J. Blade, A.J. Boulton, J. Epsztajn, A.R. Katritzky, J. Lewis, P. Molina-Buendia, Pai-Lin Nie, C.A. Ramsden, Pyridines as leaving groups in synthetic transformations: Nucleophilic displacements of amino groups, and novel preparations of nitriles and isocyanates Tetrahedron Letters. ,vol. 17, pp. 2691- 2694 ,(1976) , 10.1016/S0040-4039(00)77797-5
R. M. DODSON, J. K. SEYLER, THE REACTION OF AMIDINES WITH α,β-UNSATURATED KETONES Journal of Organic Chemistry. ,vol. 16, pp. 461- 465 ,(1951) , 10.1021/JO01143A020
Alexandru T. Balaban, Costin D. Nenitzescu, Aluminiumchlorid-Katalysen, XXVI Die Reaktion der Alkane mit Kohlenoxyd Justus Liebigs Annalen der Chemie. ,vol. 625, pp. 66- 73 ,(1959) , 10.1002/JLAC.19596250109