Arylglyoxals in Synthesis of Heterocyclic Compounds

Abstract

ZIRAK, M.; AKBARI, A.; Chem. Rev. (Washington, DC, U. S.) 113 (2013) 5, 2958-3043, http://dx.doi.org/10.1021/cr300176g ; Dep. Chem., Fac. Sci., Univ. Maragheh, Golshahr, Maragheh, Iran; Eng.) -Lindner 27-219

ZrOCl2.8H2O as a green and efficient catalyst for the expeditious synthesis of substituted 3-arylpyrimido[4,5-c]pyridazines in water

“…Exposure to pyridine has harmful effects on the liver, kidneys, immune systems and reproductive functions, and has potential carcinogenicity. [27][28][29][30][31] Following to recent reports about the application of arylglyoxals (AG) in heterocyclic chemistry, 26,[32][33][34][35][36][37][38][39][40] herein we have applied ZrOCl2•8H2O as recyclable, non-toxic and green catalyst for the regioselective synthesis of 3-arylpyrimido [4,5-c] We also studied the influence of the amount of ZrOCl2•8H2O on the reaction yields. We found that the best yield is obtained when we used the ZrOCl2•8H2O 20 mol% as a catalyst.…”

Improved Synthesis of 5-Aryl-2-thioxoimidazolidin-4-ones from Arylglyoxals Hydrates

“…Also, it must be noted that 1,5-diarylhydantoins (2b) had also been prepared by arylglyoxals condensation with Narylureas in the presence of hydrochloric acid and acetic acid in boiling ethanol for 4 h. 6 It is obviously that 1-aryl-5-arylthiohydantoins formation from arylglyoxals hydrates and thiourea takes place in the presence of strong acid [3][4][5] or in boiling acetic acid solution. 2 But the course of this reaction in acetic acid media at room temperatures has not been studied.…”

“…A structure of compound 1a is consistent with data of 1 H and 13 C NMR spectra and mass-spectrum. 2 Also, it was shown that phenylglyoxal hydrate condensed with N-arylthioureas and N-arylureas yielding 1-aryl-5-phenylthiohydantoins (2a) and 1-aryl-5-phenylhydantoins (2b) (1,5-diarylimidazolidine-2,4-diones), 3,4 respectively, in the presence of polyphosphoric acid at microwave irradiation in the absence of solvent (Scheme 1). But this method needs using of large amounts of polyphosphoric acid (or "polyphosphoric ester"…”

“…It must be noted that arylglyoxals hydrates condense with N-arylthioureas (boiling acetic acid, 4 h) and N,N'-bisarylthioureas (boiling acetic acid, 6 h) in hydrochloric acid presence yielding 1,5-diarylthiohydantoins (2a) and 1,3,5-triarylthiohydantoins (3a), 4,5 respectively (Scheme 1).…”

Synthesis of 2-{5-[4-((4-nitrophenyl)diazenyl)phenyl]-1,3,4-oxadiazol-2-ylthio}ethyl acrylate monomer and its application in a dual pH and temperature responsive soluble polymeric sensor

“…[38] It is known that poly(N-isopropylacrylamide) (PNIPAM) is one of the most important water-soluble polymers, which exhibits a heat-induced phase transition from coiled to globular state in an aqueous solution in response to temperature changes across a lower critical solution temperature (LCST) at 32°C, [39] by expanded conformation in water below the LCST due to strong hydration, and changes to compact forms above the LCST by dehydration. [40,41] Continuing our works on heterocyclic chemistry, [42][43][44][45] herein, we wish to report a new heterocyclic pH-responsive dye based on diazenylphenyl-1,3,4-oxadiazol moiety and its use in a novel water-soluble polymeric sensor, which responds to both pH and temperature.…”