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

Dengiz, Çağatay
OZCAN, Sevil
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.


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.
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, Tolga; Dengiz, Çağatay; BALCI, METİN (2017-04-01)
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 converte...
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...
A new method for the synthesis of stipitatic acid isomers: Photooxygenation of ethyl 6H-cyclohepta[d][1,3]dioxole-6-carboxylate
Dastan, A; Saracoglu, N; Balcı, Metin (2001-09-01)
Photooxygenation of the cycloheptatriene derivative 9 gave the bicyclic endoperoxide 14. Cleavage of the peroxide linkage in 14 with thiourea resulted in the formation of 16. Treatment of the endoperoxide 14 with a catalytic amount of triethylamine provided a new isomer of stipitatic acid 11, and 16. Pyrolysis or the CoTPP (TPP = tetraphenylporphyrin) catalyzed reaction of 14 resulted in the formation of iso-stipitatic acid 10, and 18,
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: