56969-73-4Relevant articles and documents
Chemoselective Synthesis of N -Arylenaminones and 3-Aroylquinolines by Synergistic Control of Temperature and Amount of Catalyst
Zhou, Pan,Hu, Biao,Rao, Kairui,Li, Lingdan,Yang, Jiao,Gao, Chuanzhu,Wang, Fengping,Yu, Fuchao
supporting information, p. 519 - 524 (2017/11/29)
An efficient and practical method has been developed for the divergent synthesis of N -arylenaminones and 3-aroylquinolines from 2-aminoaryl ketones and N, N -dimethylenaminones in the presence of 4-toluenesulfonic acid through synergistic control of the
α,β-Functionalization of saturated ketones with anthranils: Via Cu-catalyzed sequential dehydrogenation/aza-Michael addition/annulation cascade reactions in one-pot
Tiweri, Dipak Kumar,Phanindrudu, Mandalaparthi,Wakade, Sandip Balasaheb,Nanubolu, Jagadeesh Babu,Tiwari, Dharmendra Kumar
supporting information, p. 5302 - 5305 (2017/07/10)
An efficient method to access functionalized quinolines from the readily available saturated ketones and anthranils has been explored. This one-pot cascade reaction involves the in situ generation of α,β-unsaturated ketones by the copper catalysed dehydro
ZnCl2-promoted Friedl?nder-type synthesis of 4-substituted 3-aroyl quinolines from o-aminoaryl ketones and enaminones
Luo, Laichun,Zhou, Zongbao,Zhu, Jiayi,Lu, Xue,Wang, Hong
supporting information, p. 4987 - 4990 (2016/10/21)
A practical synthesis of 4-substituted 3-aroyl quinolines via Friedl?nder-type reaction from readily available o-aminoaryl ketones and enaminones was developed. In the presence of ZnCl2, the reaction proceeded smoothly affording the desired products with various functional groups in moderate to good yields.
Efficient synthesis of functionalized dihydroquinolines, quinolines and dihydrobenzo[b]azepine via an iron(iii) chloride-catalyzed intramolecular alkyne-carbonyl metathesis of alkyne tethered 2-amino benzaldehyde/acetophenone derivatives
Jalal, Swapnadeep,Bera, Krishnendu,Sarkar, Soumen,Paul, Kartick,Jana, Umasish
, p. 1759 - 1770 (2014/03/21)
In this study we have developed an efficient synthesis of 1,2-dihydroquinoline and dihydrobenzo[b]azepine derivatives involving the iron(iii) chloride intramolecular alkyne-carbonyl metathesis reaction for the first time. Various functionalized 1,2-dihydroquinolines and dihydrobenzo[b]azepines were prepared from easily accessible substrates in the presence of environmentally friendly and inexpensive iron(iii) chloride (10 mol%) under mild conditions. The method is applicable to a wide range of substrates containing different functional groups and furnishing products in good to excellent yields. This methodology was further extended to the one-pot synthesis of 3-acyl quinolines via alkyne-carbonyl metathesis/detosylation/ aromatization of N-propargyl-2-aminobenzaldehyde/acetophenone derivatives by the addition of NaOH/EtOH. While many Lewis acid and Bronsted acid catalysts were investigated, anhydrous iron(iii) chloride turned out to be the best catalyst for this transformation.
One-pot phosphine-catalyzed syntheses of quinolines
Khong, San,Kwon, Ohyun
, p. 8257 - 8267,11 (2020/10/15)
In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4- disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the β-phosphonium enoate α-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile Ntosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.
Iron-catalyzed cascade reaction of ynone with o-aminoaryl compounds: A Michael addition-cyclization approach to 3-carbonyl quinolines
Li, Hongfeng,Xu, Xiaolei,Yang, Jingyu,Xie, Xin,Huang, He,Li, Yanzhong
supporting information; experimental part, p. 530 - 533 (2011/02/28)
An efficient iron-catalyzed cascade Michael addition-cyclization of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones, and o-aminobenzyl alcohols with ynones for the synthesis of 3-carbonyl quinolines is reported. The reactions proceed to afford 3-carbonyl quinoline derivatives with or without substituent at the C-4 position in good to high yields using Iron(III) chloride hexahydrate as the catalyst in the air.
