13180-36-4Relevant articles and documents
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.
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 (2007/10/03)
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.
Further insight into the reactivity of oxazinones toward phosphorus reagents
Abdou, Wafaa M.,Kamel, Azza A.,Khidre, Maha D.
, p. 4119 - 4134 (2007/10/03)
A series of quinoline derivates has been obtained from the reaction of 3-phenyl-2,4-benzoxazin-1-one (1) with alkylidenephosphoranes. With ester ylides 3a,b, the reaction affords hydroxyquinolines 8a,b and new stable phosphorus ylide 9, whereas with keto ylides 3c,d, quinolinones 12a,b, hydroxyindoles 10a,b and benzoazepines 14a,b are obtained. 1 reacts with allyl-4, methyl-5a and ethyltriphenylphosphonium bromides 5b in the presence of LiH to afford 2-hydrophenyloxazolo[1,2-a]-4-hydroxyquinoline (16) from the first reaction whereas alkoxyquinolines 21a,b and hydroxyazepines 22a,b are obtained from 5a,b.
