1483-31-4Relevant academic research and scientific papers
Deaminative chlorination of aminoheterocycles
Ghiazza, Clément,Faber, Teresa,Gómez-Palomino, Alejandro,Cornella, Josep
, p. 78 - 84 (2021/12/23)
Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]
Transition-metal-free oxidative iodination of 1,3,4-oxadiazoles
Dannenberg, Carl Albrecht,Bizet, Vincent,Zou, Liang-Hua,Bolm, Carsten
supporting information, p. 77 - 80 (2015/02/02)
Transition-metal-free oxidative iodination of 2-substituted 1,3,4-oxadiazoles was achieved by using sodium iodide as the halide source and Selectfluor as the oxidant. Variously substituted products were obtained in moderate to good yields under operationa
Synthesis, antibacterial evaluation and QSAR studies of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolone derivatives
Kumar, Rajnish,Kumar, Ashwani,Jain, Sandip,Kaushik, Darpan
, p. 3543 - 3550 (2011/10/19)
A series of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolones (I-XXI) were synthesized using an appropriate synthetic route and characterized by elemental and spectral analysis. The antibacterial activities of all the synthesized compounds were e
Trimethylsilyl-1,3,4-oxadiazoles-new useful synthons for the synthesis of various 2,5-disubstituted-1,3,4-oxadiazoles
Zarudnitskii, Evgenij V.,Pervak, Igor I.,Merkulov, Anatolij S.,Yurchenko, Aleksandr A.,Tolmachev, Andrej A.
, p. 10431 - 10442 (2008/12/23)
The reactivity of 2-aryl-5-trimethylsilyl-1,3,4-oxadiazoles toward different types of electrophiles was investigated. These silanes readily react with chlorine, bromine, aliphatic acyl chlorides, 2-nitrobenzenesulfenyl chloride, and some reactive isocyana
Synthesis of Some New 5-Aryl/Aryloxymethyl-2-Chloro-1,3,4-Oxadiazoles and their Oxadiazoloquinazolone Derivatives as Potential Pesticides
Singh, H.,Yadav, L. D. S.,Bhattacharya, B. K.
, p. 436 - 439 (2007/10/02)
Several 5-aryl/aryloxymethyl-2-chloro-1,3,4-oxadiazoles (III) have been prepared by treating 2-aryl/aryloxymethyl-Δ2-1,3,4-oxadizolin-5-ones (IIa) with POCl3/PCl5.The latter were prepared by cyclisation of their corresponding N-aroylaryloxyacet
