Synthesis of Indolin-2-one, Isoindolin-1-one, and Indole Derivatives from Homophthalic Acid

Date

2011-11-01

Author

KILIKLI, Alper A.
Dengiz, Çağatay
OZCAN, Sevil
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

168
views

0
downloads

We hereby report the preparation of indolin-2-one and isoindolin-1-one and their derivatives starting from 2-(carboxymethyl)benzoic acid, which was first regiospecifically converted into the isomeric half esters. Transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the regioisomeric isocyanates. Reaction of the isocyanates with aniline produced urethane derivatives. Intramolecular cyclization provided the target compounds.

Subject Keywords

Amides, Azides, Fused-ring systems, Heterocycles, Indoles

URI

https://hdl.handle.net/11511/35566

Journal

SYNTHESIS-STUTTGART

DOI

https://doi.org/10.1055/s-0030-1260235

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of new 4-aza-indoles via acyl azides Dogan, Sengul Dilem; DEMİRPOLAT, Eren; Aycan, Mukerrem Betul Yerer; Balcı, Metin (Elsevier BV, 2015-01-14) We hereby report the preparation of new azaindole derivatives starting from 2-(2-ethoxy-2-oxoethyl) nicotinic acid. Conversion of a half ester into acyl azide followed by Curtius rearrangement gave the corresponding isocyanate. Trapping of the isocyanate with different nucleophiles produced urea and urethane derivatives. Intramolecular cyclization reactions gave the target compounds.
Synthesis of Furo[2,3-d]pyridazin-4(5H)-one and Its N(5)-Substituted Derivatives Karahan, Emrah; Koza, Gani; Balcı, Metin (2014-11-01) We report the efficient preparation of furo[2,3-d] pyridazin-4(5H)-one and its N-substituted derivatives starting from methyl 2-methylfuran-3-carboxylate. The Me group was converted to the aldehyde group, which was then condensed with hydrazine derivatives. Then, the ester functionalities were hydrolyzed to the corresponding acids, followed by treatment with SOCl2 to give N-substituted furopyridazinone derivatives.
Regioselective Synthesis of the 5,6-Dihydro-4H-furo[2,3-c]pyrrol-4-one Skeleton: A New Class of Compounds Koza, Gani; Karahan, Emrah; Balcı, Metin (Wiley, 2010-01-01) We hereby report the first preparation of the 5,6-dihydro-4H-furo[2.3-c]pyrrol-4-one (3) and its derivatives starting from methyl 3-(methoxycarbonyl)furnan-2-acetate (8). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9. Conversion of 9 into the acyl azide In followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 (Scheme 2). Reaction of 11 with different nucleophiles produced urethane and urea derivatives (Sche...
Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure Ekmekci, Zeynep; Balcı, Metin (2012-09-01) A new 2,3-diaminoconduritol derivative with the conduritol F structure was prepared starting from cyclohexa-1,4-diene. Initially, a lactam, prepared by the cycloaddition of chlorosulfonyl isocyanate (CSI) to cyclohexa-1,4-diene, was converted into an amino acid. The conversion of the acid functionality into an isocyanate resulted in the formation of an imidazolidinone derivative, formed by an intramolecular cyclization. In the second part of this work, the known anhydride, 3a,4,7,7a-tetrahydroisobenzofuran-...
Fabrication and analysis of dye-sensitized solar cells (DSSCs) using porphyrin dyes with catechol anchoring groups Adineh, Maryam; Tahay, Pooya; Ameri, Mohsen; Safari, Nasser; Mohajerani, Ezeddin (2016-01-01) Herein we report the preparation and application of 4 different zinc(II) tetrakis(dihydroxyphenyl) porphyrins (ZnTDHPP) as the sensitizing dyes in dye-sensitized solar cells (DSSCs). The experimental results include solution and solid state UV-Vis data, steady state current-voltage characteristics, and our theoretical analysis comprised of density functional theory (DFT) and Langmuir isotherm adsorption formalism. The results show that the Zn tetrakis(2,3-dihydroxyphenyl) porphyrin (Zn2,3TDHPP) and Zn tetra...

Citation Formats

A. A. KILIKLI, Ç. Dengiz, S. OZCAN, and M. BALCI, “Synthesis of Indolin-2-one, Isoindolin-1-one, and Indole Derivatives from Homophthalic Acid,” SYNTHESIS-STUTTGART, pp. 3697–3705, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35566.