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

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

161
views

0
downloads

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

Suggestions

OpenMETU
Core

The preparation and characterization of gold(0) nanoclusters stabilized by zeolite framework: Highly active, selective and reusable catalyst in aerobic oxidation of benzyl alcohol Zahmakiran, Mehmet; Özkar, Saim (2010-05-15) Zeolite framework stabilized gold(0) nanoclusters were prepared by the ion-exchange/impregnation of Au3+ ions with zeolite-Y followed by reduction of the Au3+ ions using sodium borohydride in aqueous solution, all at 50 degrees C. The zeolite framework stabilized gold(0) nanoclusters were isolated as red powder and characterized by HR-TEM, TEM, TEM-EDX, XRD, XPS, DR-UV-vis, SEM, ICP-OES spectroscopic methods and N-2-adsorption technique. This new material was found to be highly active, selective and reusabl...
THE OXIDATION OF BETA-ALKOXYCYCLOPENTENONES AND BETA-ALKOXYCYCLOHEXENONES TO ALPHA'-ACYLOXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS Demir, Ayhan Sıtkı; SAYRAC, T; WATT, DS (1990-12-01) The alpha-oxidation of cyclic derivatives of beta-alkoxy-alpha, beta-unsaturated ketones using manganese (III) acetate in the presence of various carboxylic acids provided a convenient synthesis of 5-acyloxy-3-alkoxy-2-cyclopentenones and 6-acyloxy-3-alkoxy-2-cyclohexenones.
The synthesis and sodium-silver ion exchange of sodalites Acar, Aybar Can; Culfaz, A (2003-05-01) Aluminosilicate sodalites of three different types-chlorosodalite, basic sodalite, and oxalate sodalite-have been synthesized in their sodium forms using hydrothermal synthesis. The syntheses were investigated in terms of their relative rates of crystallization and final crystallinities using powder X-ray diffraction. These sodalites were subsequently loaded with silver by aqueous ion exchange. The exchange was studied primarily by monitoring the solution phase. Rate of exchange and equilibrium behavior hav...
The use of n-polyethereal polypyrroles in preconcentration and surface enhanced raman scattering studies Köksel, Bahar; Volkan, Mürvet; Department of Chemistry (2009) Polypyrroles containing polyether pseudocages (PI, PII, PIII) have been synthesized via chemical oxidation of 1,5-bis(1,1-pyrrole)-3-oxabutane (MI), 1,8- bis(1,1-pyrrole)-3,6-dioxahexane (MII), and 1,11-bis(1,1-pyrrole)- 3,6,9-trioxaundecane (MIII) using anhydrous FeCl3 in CHCl3. Because as obtained polymer resins did not give any response toward any cations, they were reduced (undoped) using chemical reducing agents. Tetrabutylammonium hydroxide (TBAOH) was found to be more effective in undoping to obtain ...
A novel class of compounds: synthesis of 5,5 '-carbonyl-bis(5,6-dihydro-4H-furo- and thieno-[2,3-c]pyrrol-4-ones) KOZA, GANİ; Balcı, Metin (2011-11-11) We hereby report the first synthesis of novel class of compounds, 5,5'-carbonyl-bis(5,6-dihydro-4H-thieno- and furo-[2,3-c]pyrrol-4-one starting from methyl 2-(2-methoxy-2-oxoethyl) thiophene- and furan-3-carboxylate, respectively. The ester functionalities connected to methylene group were regiospecifically converted to the desired monoacyl azides. Curtius rearrangement of acyl azides followed by hydrolysis of the formed isocyanates gave the symmetrical urea derivatives. Cyclization of the ester groups pro...

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.