2011
DOI: 10.1016/j.tet.2011.03.040
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α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones

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Cited by 18 publications
(10 citation statements)
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“…Pyrazoles 8 were synthesized from cyanoacetic acid derivative 5 through intermediates 6 and 7 by adopting previously published protocols …”
Section: Methodsmentioning
confidence: 99%
“…Pyrazoles 8 were synthesized from cyanoacetic acid derivative 5 through intermediates 6 and 7 by adopting previously published protocols …”
Section: Methodsmentioning
confidence: 99%
“…This has been the basis for synthetic methodologies leading to halogen-substituted ketones, 2 aminoketones, 3 N -heterocyclic ketones, 3 and other products. 4 Likewise, Shudo and Ohwada have described a superacid-promoted Houben-Hoesch reaction in which dicationic species are formed and these superelectrophilic conversions are shown give good yields aryl ketones. 5 …”
Section: Introductionmentioning
confidence: 99%
“…According to literature, it has been reported that 2-cyanoacrylamide derivatives were obtained by reacting cyanoacetamide with DMFDMA in toluene at 90 °C for 1-4 h with molar ratio 1:2 [49]. In the present investigation, the desired 2-cyano-acrylamides 2a-c were prepared according to the previously mentioned procedure, but with decreasing the quantity of DMFDMA to (1.1eq) and increasing the reaction time to 7 h. The reaction mixture revealed the presence of a by-product (by TLC) which supposed to be the dimer 3a-c because its mass has almost twice as the desired product.…”
Section: Chemistrymentioning
confidence: 99%