A convenient approach to the synthesis of substituted 2-(methylamino)quinoline-3-carboxamides

Authors

  • L. V. Muzychka Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • O. B. Smolii Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • I. I. Biletskiy Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • O. M. Vasilenko Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.15.855

Keywords:

condensation, pyrimido[4, 5-b]quinoline-2, 4(1H, 3H)-dione, 5-deazaalloxazine, 2-(methylamino)quinoline- 3-carboxamide

Abstract

The paper is devoted to the synthesis of new 2-(methylamino)quinoline-3-carboxamide derivatives by the pyrimidine cycle hydrolytic cleavage of pyrimido[4,5-b]quinoline-2,4(1H,3H)-diones. These later were synthetized in high yields by interaction of available 1,3-dimethyl-6-piperidinyl-5-formyluracil with aromatic amines. The reactions with participation of ortho- and para-substituted aromatic amines proceed regioselectively to give 1,3-dimethylpyrimido[4,5-b] quinoline-2,4(1H,3H)-diones with substituents in positions 7 and 9 of the heterocycle. The use of metha-methoxyand metha-fluoroaniline leads to the mixture of 6- and 8-substituted 1,3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)- diones, which under basic conditions were cleaved into amides of quinoline-3-carboxylic acid. The mixture of 2-(methylamino)quinoline-3-carboxamides obtained was separated by column chromatography. Application of the correlation NMR spectroscopy method (NOESY, COSY, HSQC, HMBC) has allowed to reliably determine the structures of 1,3-dimethyl-5-formyluracil derivatives with aromatic amines condensation products. The amino-imino prototropic tautomerism occurs at 120°C. It facilitates syn-anti-isomerization promoted cyclization and leads to 1,3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)-dione. The structure of the compounds obtained has been proven using the methods of NMR 1 Н, 13C-spectroscopy, mass-spectra and elemental analysis.

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Published

2015-09-10

How to Cite

(1)
Muzychka, L. V.; Smolii, O. B.; Biletskiy, I. I.; Vasilenko, O. M. A Convenient Approach to the Synthesis of Substituted 2-(methylamino)quinoline-3-Carboxamides. J. Org. Pharm. Chem. 2015, 13, 70-78.

Issue

Vol. 13 No. 3(51) (2015)

Section

Original Researches

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