Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones

Koza, Gani
Keskin, Selbi
Ozer, Merve Sinem
Cengiz, Betul
ŞAHİN, Ertan
Balcı, Metin
We hereby report the synthesis of a novel class of compounds, 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones starting from methyl 2-(2-methoxy-2-oxoethyl)furan- and thiophene-3-carboxylate and methyl 2-(2-methoxy-2-oxoethyl)benzoate. The ester functionalities connected directly to the aromatic ring were regiospecifically converted to the acid, whereas methylene groups were oxidized to the corresponding ketoesters. Reaction of the ketoesters with hydrazine provided the hydrazone derivatives. An intramolecular cyclization in the presence of thionyl chloride formed a fused pyridazinone skeleton. Hydrolysis of the remaining ester groups and transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the isocyanates. Reaction of the isocyanates with methanol and water produced urethane and amino-pyridazinone derivatives, respectively.


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...
Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs
Demir, Ayhan Sıtkı; Sesenoglu, O; Ulku, D; Arici, C (Wiley, 2004-01-01)
Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields. Cyclopropanation of the C=C bond with trimethylsulfoxonium iodide (Me3SO+I-) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90-97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stercoselective reduction of the C-N bond followed by separation of the formed diastereoisomers, furnished (2-arylcy...
Polycyclic aromatic hydrocarbon-substituted push-pull chromophores: an investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches
Dengiz, Çağatay (2021-01-01)
A series of new push-pull chromophores were synthesized in moderate to very high yields (65%-97%) by treating TCNE and TCNQ with alkynes substituted by electron-rich diethylaniline and polycyclic aromatic hydrocarbons. Some of the chromophores exhibit strong intramolecular charge-transfer bands in the near-1R region with lambda(max). values between 695 and 749 nm. With the help of experimental and theoretical analysis, it is concluded that the trend in lambda(max) values is affected by PAH substituents ster...
Enantioselective reduction of ketones with borane catalyzed by cyclic β- amino alcohols prepared from proline
Demir, Ayhan S; Mecitoglu, Idris; Tanyeli, Cihangir; Gülbeyaz, Volkan (Elsevier BV, 1996-12)
New catalysts have been prepared from (S)- and (R)- proline and the asymmetric borane reduction of prochiral ketones using these catalysts has been studied. The secondary alcohols were obtained in 76-95% yield with 57-96% enantiomeric excesses. Copyright (C) 1996 Elsevier Science Ltd
Aryl butenoic acid derivatives as a new class of histone deacetylase inhibitors: synthesis, in vitro evaluation, and molecular docking studies
Esiyok, Peruze Ayhan; Seven, Ozlem; Eymur, Guluzar; Tatar, Gamze Bora; DAYANGAÇ ERDEN, DİDEM; YELEKÇİ, Kemal; YURTER, HAYAT; Demir, Ayhan Sıtkı (The Scientific and Technological Research Council of Turkey, 2014-01-01)
New aryl butenoic acid derivatives have been synthesized by combining hydroxy- or methoxy-substituted phenyl rings as the capping group, with a double bond in the short linker as well as metal binding groups, enoic ester, and salts bearing either methyl or morpholine. These compounds have been shown to possess promising histone deacetylase inhibition activities via in vitro fluorometric assay and molecular docking studies.
Citation Formats
G. Koza, S. Keskin, M. S. Ozer, B. Cengiz, E. ŞAHİN, and M. Balcı, “Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones,” TETRAHEDRON, pp. 395–409, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51896.