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Paper | Special issue | Vol 93, No. 1, 2016, pp.150-163
Published online, 20th October, 2015
DOI: 10.3987/COM-15-S(T)12
Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions

Vilija Kriščiūnienė, Gita Matulevičiūtė, Osvaldas Paliulis, Patrick Rollin, and Algirdas Šačkus*

*Institute of Synthetic Chemistry, Kaunas University of Technology, Radvilėnų Rd. 19, LT-50270 Kaunas, Lithuania


With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr·Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.