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One-pot three components effective methods are reported for the synthesis of two important families of organic compounds, 2 H -pyrrolo[2,3- d ]pyrimidine-2,4(3 H )-diones substituted 5-(3-hydroxy-1,4-naphthoquinonyl) and 1 H -benzo[ f ]indole-4,9-diones substituted 3-(3-hydroxy-1,4-naphthoquinonyl), by employment of new starting materials. The formers were prepared  via  the one-pot condensation reaction between phenylglyoxal, 2-hydroxynaphtoquinone and 2-amino-1,4-naphthoquinone derivatives and the later through the reaction of phenylglyoxal, 2-hydroxy naphthoquinone and 2-amino-1,4-naphthoquinone derivatives. The reaction medium for the synthesis of both procedures was acetic acid/water (1:1; v/v) at 100 °C, and various derivatives of these compounds were obtained with high-efficiency and identified by their IR,  1 H- and  13 C-NMR spectra. In spite of their apparent planar structures, the NMR spectra of some products shown asymmetric properties of CH 2  protons or existence of two diastereomers due to restriction of C hydroxyquinoline ˗C pyrrol  bonds, together with formation of relatively stable nonplanar eight membered ring resulted from hydrogen bond formation between hydroxynapthoquinone’s OH and carbonyl groups of uracil motifs.

polycyclic aromatic compounds

New One-Pot Pathway for the Synthesis of 2 H –Pyrrolo[2,3- d ]Pyrimidine-2,4-(3 H )-Diones and 1 H -Benzo[ f ]Indole-4,9-Dione Derivatives Substituted 3-Hydroxy-1,4-Naphthoquinonyl