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

Date

2017-04-01

Author

KAPTI, Tolga
Dengiz, Çağatay
BALCI, METİN

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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.

Subject Keywords

Oxidation, Indole, Heterocycles, Condensation, Azides

URI

https://hdl.handle.net/11511/40620

Journal

SYNTHESIS-STUTTGART

DOI

https://doi.org/10.1055/s-0036-1588119

Collections

Department of Chemistry, Article

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Citation Formats

T. KAPTI, Ç. Dengiz, and M. BALCI, “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,” SYNTHESIS-STUTTGART, pp. 1898–1904, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40620.