The Chemistry of Ethyl 3-(2-Ethoxy-2-oxoethyl)-1H-indole-2-carboxylate: Synthesis of Pyrimido[4,5-b]indoles and Diethyl 4-Hydroxyquinoline-2,3-dicarboxylate via Intramolecular Cyclizations

KAPTI T., DENGİZ Ç., BALCI M.

SYNTHESIS-STUTTGART, cilt.49, sa.8, ss.1898-1904, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 49 Sayı: 8
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1055/s-0036-1588119
  • Dergi Adı: SYNTHESIS-STUTTGART
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1898-1904
  • Anahtar Kelimeler: azides, condensation, heterocycles, indole, oxidation, RECEPTOR TYROSINE KINASE, INDOLE-DERIVATIVES, WINTERFELDT-OXIDATION, BIOLOGICAL-ACTIVITY, INHIBITORS, RIBONUCLEOSIDES, POTENT, AGENTS, CELLS
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

We report the synthesis of a new series of 2-oxo-1,2,4,9-tetrahydro- 3H-pyrimido[4,5-b] indole derivatives and diethyl 4-hydroxyquinoline- 2,3-dicarboxylate starting from ethyl 3-(2-ethoxy-2-oxoethyl)- 1H-indole-2-carboxylate. Intramolecular cyclization formed the target ring systems. The key substrates featuring both acyl azide and isocyanate functionalities were prepared from bis(acyl azide) intermediate. The acyl azide functionalities directly connected to methylene groups were regiospecifically converted into urea and urethanes via the reactive isocyanate intermediates. Thermal treatment of urea and urethanes provided the target 2-oxo-1,2,4,9-tetrahydro-3H-pyrimido[4,5b] indoles. Furthermore, ozonolysis of the starting indolediester substrate and subsequent base treatment to diethyl 4-hydroxyquinoline-2,3-dicarboxylate are described.