36684-33-0Relevant academic research and scientific papers
Regioselective condensation of alkylidenephosphoranes with bifunctionalized compounds: New approach to the synthesis of fused O- and N-heterocycles
Abdou, Wafaa M.,Ganoub, Neven A. F.,Fahmy, Amin F. M.,Shaddy, Abeer A. M.
, p. 2373 - 2390 (2005)
A series of fused pyran- (～40% yield) and furan- (～20% yield) derivatives were regioselectively prepared from the reactions of 5,6-difur-2′yl-3-oxo-2,3-dihydropyridazin-4-carbonitrile with ester- and keto phosphorus ylides, whereas new ylides were obtained, in addition to fused furans, in almost equal yields (33%) from the reaction of the same substrate with cyanomethylene(triphenyl)phosphorane. However, application of such Wittig reagents on 2-[(benzylidene)amino]-benzonitrile afforded, in all cases, 4-hydroxyquinolines in a ～42% yield as major products. Moreover, 2-[(triphenylphosphoranylidene)amino] benzonitrile, with the corresponding alkene, was also isolated a side products. Copyright Taylor & Francis Inc.
Cascade Knoevenagel and aza-Wittig reactions for the synthesis of substituted quinolines and quinolin-4-ols
Zhang, Xiaofeng,Ma, Xiaoming,Qiu, Weiqi,Evans, Jason,Zhang, Wei
, p. 349 - 354 (2019/01/28)
A [4 + 2] annulation involving cascade Knoevenagel, aza-Wittig and dehydrofluorination reactions is developed for the synthesis of substituted quinolin-4-ols including analogs bearing CF2H, CF3, and C2F5 groups. This simple and highly efficient method is also applicable for the synthesis of substituted quinolines. A number of reported biologically active compounds can be readily prepared by this one-pot synthesis. Green chemistry metrics analysis of the new reaction processes provided favorable results.
