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

Abstract

One-pot three components effective methods are reported for the synthesis of two important families of organic compounds, 2H-pyrrolo[2,3-d]pyrimidine-2,4(3H)-diones substituted 5-(3-hydroxy-1,4-naphthoquinonyl) and 1H-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, ¹H- and ¹³C-NMR spectra. In spite of their apparent planar structures, the NMR spectra of some products shown asymmetric properties of CH₂ 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.

Keywords:

• Phenylglyoxal
• 2-hydroxy-1,4-naphthoquinone
• 2-amino-1,4-naphthoquinones
• pyrrolo[2,3-d]pyrimidinones
• benzo[f]indole-4,9-diones

Acknowledgements

The authors thank the Research Council of the Persian Gulf University of Bushehr for financial support of this work

Disclosure statement

No potential conflict of interest was reported by the authors.