56656-34-9Relevant academic research and scientific papers
Synthesis of 4-(5-Nitrophenylfur-2-yl)-1,2,3-thia- and Selenadiazoles
Dmiterko,Pevzner,Petrov,Zavgorodnii
, p. 701 - 707 (2019/06/27)
Arylation of 2-acetylfuran with o-, m-, and p-nitrophenyldiazonium salts under the conditions of the Gomberg-Bachmann reaction has afforded the corresponding 5-(nitrophenyl)-2-acetylfurans. Their carbo-ethoxyhydrazones have undergone the cyclization into stable 4-(5-nitrophenylfur-2-yl)-1,2,3-thiadiazoles under the conditions of the Hurd-Mori reaction. Analogous semicarbazones have afforded the corresponding selenadiazoles upon oxidation with selenium dioxide. The analysis of electronic absorption spectra of the obtained hybrid heterocycles has shown that the conjugation of the phenyl and the furan ring in o-nitrophenyl derivatives is distorted due to steric hindrance, whereas the effect of direct polar conjugation leading to strong bathochromic shift of the absorption band has been observed in the case of the p-nitro derivatives. The position and intensity of the bands in the electronic absorption spectra of the studied compounds are determined by electronic as well as steric factors. The difference in the length of conjugation chain determined by the position of the nitro group in the phenyl fragment also contributes to the observed trend. The introduction of selenadiazole fragment instead of thiadiazole one has caused slight bathochromic shift of the band in the electron absorption spectra.
Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast
Trif, Maria,Kall, Noemi Hajnalka,Naghi, Mara Ana,Bencze, Laszl Csaba
experimental part, p. 177 - 183 (2012/06/30)
Baker's yeast mediated reduction of various phenylfuran-2-yl-ethanones has been studied. The influence of the reaction conditions, the type and position of the substituents, as well the presence of various additives on the enantiomeric composition of the products and the reaction yield are discussed. The absolute configuration of the reaction products was established using a retrosynthetic procedure.
Substituent effects on the stereochemical outcome of the baker's yeast-mediated biotransformation of α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones
Bencze, Laszlo Csaba,Paizs, Csaba,Tosa, Monica Ioana,Irimie, Florin Dan
experimental part, p. 356 - 364 (2010/06/16)
In this Letter the baker's yeast-mediated biotransformation of variously substituted α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones is described. The stereochemical outcome of the reactions was strongly influenced by the nature of the substituents on the phenyl ring.
A new simple route to the thieno[2,3-b]indole ring system
Butin, Alexander V.,Tsiunchik, Fatima A.,Abaev, Vladimir T.,Zavodnik, Valery E.
experimental part, p. 1145 - 1148 (2009/04/06)
A simple and effective method has been elaborated for the synthesis of thieno[2,3-b]indole ring system. It is based on the electrophilic recyclization of 2-alkyl-5-(2-isothiocyanoaryl)furans in the presence of anhydrous AlCl 3. Georg Thieme Ver
Furan as a 1,3-diketone equivalent: the second type furan recyclization applied to indole synthesis
Butin, Alexander V.
, p. 4113 - 4116 (2007/10/03)
A new approach for the synthesis of indole derivatives based on protolytic recyclization of 2-alkyl-5-(2-tosylaminoaryl)-furans is described. The furan ring in this unusual transformation formally serves as a 1,3-diketone equivalent.
