Synthesis of Furo[2,3-d]pyridazin-4(5H)-one and Its N(5)-Substituted Derivatives

Date

2014-11-01

Author

Karahan, Emrah
Koza, Gani
Balcı, Metin

Metadata

Show full item record

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

Item Usage Stats

180
views

0
downloads

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.

Subject Keywords

Phthalazinones , Pyridazines , Furans, Pyrroles

URI

https://hdl.handle.net/11511/57382

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.201400042

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis, structural characterization and chemistry of tribenzoheterotriquinane based molecular structures. Kepil, Dilay; Günbaş, Emrullah Görkem; Department of Chemistry (2020) The synthesis of heteroatom containing derivatives of triquinane structure by the Mascal group represents an important development in the field of fundamental organic chemistry. Some derivatives of hererotriquinane structures showed unusual reactivity and structure properties. For example, oxonium ions are known as fleeting intermediates in certain reaction mechanisms. However, oxatriquinane, the oxygen containing analogue of heterotriquinane family, shows extreme stability. It can be chromatographed and su...
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 Indolin-2-one, Isoindolin-1-one, and Indole Derivatives from Homophthalic Acid KILIKLI, Alper A.; Dengiz, Çağatay; OZCAN, Sevil; BALCI, METİN (2011-11-01) 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 ferrocenyl quinones and ferrocenyl based burning rate catalysts Açıkalın, Serdar; Zora, Metin; Department of Chemistry (2003) Recently, considerable interest has been devoted to the synthesis of new ferrocene derivatives since properly functionalized ferrocene derivatives could be potential antitumor substances. For this purpose, we have investigated the synthesis of ferrocenyl quinones starting from squaric acid. Thermolysis of ferrocenylsubstituted cyclobutenones, which have been prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl c...
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...

Citation Formats

E. Karahan, G. Koza, and M. Balcı, “Synthesis of Furo[2,3-d]pyridazin-4(5H)-one and Its N(5)-Substituted Derivatives,” HELVETICA CHIMICA ACTA, pp. 1487–1496, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57382.