40941-54-6Relevant articles and documents
Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes
Xu, Jincheng,Li, Yang,Ding, Tianling,Guo, Hao
supporting information, p. 3114 - 3117 (2021/09/03)
A convenient protocol for the synthesis of quinoline-4-carbaldehydes via chemoselective oxidation of 4-methylquinolines using hypervalent iodine(III) reagents as oxidant is described. This method highlights metal-free and mild reaction conditions, nice yield, good functional group tolerance, and high chemoselectivity.
Synthesis and antileishmanial evaluation of thiazole orange analogs
Abdelhameed, Ahmed,Liao, Xiaoping,McElroy, Craig A.,Joice, April C.,Rakotondraibe, Liva,Li, Junan,Slebodnick, Carla,Guo, Pu,Wilson, W. David,Werbovetz, Karl A.
supporting information, (2019/11/28)
Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.
Palladium-catalyzed aerobic oxidative coupling of allylic alcohols with anilines in the synthesis of nitrogen heterocycles
Kumar, Gangam Srikanth,Singh, Diksha,Kumar, Manish,Kapur, Manmohan
, p. 3941 - 3951 (2018/04/14)
We report herein an unprecedented and expedient Pd-catalyzed oxidative coupling of allyl alcohols with anilines to afford β-amino ketones which are converted into substituted quinolines in a one-pot fashion. The exclusive preference for N-alkylation over N-allylation makes this approach unique when compared to those reported in literature. Detailed mechanistic investigations reveal that the conjugate addition pathway was the predominant one over the allylic amination pathway. The notable aspects of the present approach are the use of readily available, bench-stable allyl alcohols and molecular oxygen as the terminal oxidant, in the process dispensing the need for unstable and costly enones. Further, we explored the synthetic utility of β-amino ketones through an intramolecular α-arylation methodology and a one-pot domino annulation, thereby providing rapid access to indolines and quinolines.
Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts
Khusnutdinov,Bayguzina,Aminov
, p. 1613 - 1618 (2016/08/26)
2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.
Solvent-promoted and -controlled Aza-Michael reaction with aromatic amines
De, Kavita,Legros, Julien,Crousse, Benoit,Bonnet-Delpon, Daniele
experimental part, p. 6260 - 6265 (2009/12/06)
(Chemical Equation Presented) 1,4-Addition of anilines onto Michael acceptors proceeds easily in specific polar protic solvents, without any promoting agent. According to the solvent and to the electrophile, the selectivity of the reaction can be finely tuned. With methyl acrylate as electrophile, only monoaddition takes place in water, while the diadduct is yielded in hexafluoroisopropyl alcohol (HFIP). The use of methyl vinyl ketone as a partner affords the monoadduct in water, the diadduct in trifluoroethanol (TFE), and the quinoline in HFIP.
Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions
Ranu, Brindaban C.,Hajra, Alakananda,Dey, Suvendu S.,Jana, Umasish
, p. 813 - 819 (2007/10/03)
A convenient and efficient procedure for the synthesis of quinolines and dihydroquinolines has been developed by a simple one-pot reaction of anilines with alkyl vinyl ketones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent.
Microwave-assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride
Ranu, Brindaban C.,Hajra, Alakananda,Jana, Umasish
, p. 531 - 533 (2007/10/03)
A simple and efficient procedure has been developed for the synthesis of 4-alkylquinolines by a one-pot reaction of anilines with alkyl vinyl ketones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent.
