102145-14-2Relevant academic research and scientific papers
The development of efficient protocols for the palladium-catalyzed cyclization reactions of secondary amides and carbamates
Yang, Bryant H.,Buchwald, Stephen L.
, p. 35 - 37 (1999)
(equation presented) With the proper choice of palladium catalyst, ligand, and base, five-, six-, and seven-membered rings are formed efficiently from secondary amide or secondary carbamate precursors, offering significant improvements to currently existing methodology.
Visible-Light Induced C(sp2)?H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover
Chang, Sukbok,Jeong, Jiwoo,Jung, Hoimin,Keum, Hyeyun,Kim, Dongwook
, p. 25235 - 25240 (2021/10/25)
We report an approach for the intramolecular C(sp2)?H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C?C bond migration.
Synthesis of Chiral 2-Substituted 1,4-Benzoxazin-3-ones via Iridium-Catalyzed Enantioselective Hydrogenation of Benzoxazinones
Nie, Yu,Li, Jing,Yan, Jun,Yuan, Qianjia,Zhang, Wanbin
supporting information, p. 5373 - 5377 (2021/07/26)
An efficient iridium-catalyzed enantioselective hydrogenation of 2-alkylidene 1,4-benzoxazin-3-ones using our developed iPr-BiphPHOX as a ligand is reported. This method showed good functional group compatibility and delivered the corresponding reduced products in excellent yields (up to 99%) with excellent enantioselectivities (up to 99% ee). The reaction proceeded very well on a gram scale with low catalyst loadings (0.1 mol %), providing the product with no erosion in enantioselectivity. Additionally, three bioactive molecules can be easily obtained from the reduced products.
Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1 H)-one Derivatives via Hydride Transfer/ N-Dealkylation/ N-Acylation
Hu, Fangzhi,Li, Sanming,Li, Shuai-Shuai,Wang, Liang,Xu, Lubin,Yang, Xiaoyu
supporting information, p. 358 - 364 (2021/01/13)
The switchable synthesis of 3-non, 3-mono, 3,3′-disubstituted 3,4-dihydroquinolin-2(1H)-ones was developed through a redox-neutral hydride-transfer/N-dealkylation/N-acylation strategy from o-aminobenzaldehyde with 4-hydroxycoumarin, and Meldrum's acid, respectively. The unprecedented strategy for the synthesis of 3,3′-highly functionalized 3,4-dihydroquinolin-2(1H)-one has been realized with the in situ utilization of the released HCHO via the o-QM involved Michael addition. In addition, the synthetic utility of this protocol has been well illustrated via concise synthesis of CYP11B2 inhibitor.
NIS-mediated oxidative arene C(sp2)-H amidation toward 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam derivatives
Wu, Lingang,Hao, Yanan,Liu, Yuxiu,Wang, Qingmin
, p. 6762 - 6770 (2019/07/22)
A new radical-mediated intramolecular arene C(sp2)-H amidation of 3-phenylpropanamides or [1,1′-biphenyl]-2-carboxamides was developed to prepare a series of 3,4-dihydro-2(1H)-quinolinone and phenanthridone derivatives in moderate to excellent yields (33-94%). Spirolactams could also be obtained using this protocol.
Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines
Chisholm, David R.,Zhou, Garr-Layy,Pohl, Ehmke,Valentine, Roy,Whiting, Andrew
supporting information, p. 1851 - 1862 (2016/10/05)
The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.
Synthesis of novel phenylnaphthyl phosphines and their applications to Pd-catalyzed intramolecular amidation
Kitamura, Yuki,Hashimoto, Ayano,Yoshikawa, Seiji,Odaira, Jun-Ichi,Furuta, Takumi,Kan, Toshiyuki,Tanaka, Kiyoshi
, p. 115 - 117 (2007/10/03)
Novel phenylnaphthyl phosphines were prepared and applied to the Pd-catalyzed intramolecular amidation. Both ligands gave good to excellent yields in the synthesis of five-, six-, and seven-membered rings from halo-amides and carbamates. Georg Thieme Verl
Intramolecular palladium-catalyzed aryl amination and aryl amidation
Wolfe, John P.,Rennels, Roger A.,Buchwald, Stephen L.
, p. 7525 - 7546 (2007/10/03)
Upon treatment with a palladium catalyst and a suitable base, aromatic halides undergo intramolecular substitution to form five, six, and seven-membered rings. In a similar fashion aryl halides with pendant amides or sulfonamides are cyclized to form five and six-membered rings.
Synthesis of 3,4-dihydroisoquinolines, 2-alkyl(acyl)-1(2H)-3,4-dihydroisoquinolinones, 2-alkyl-1(2H)-isoquinolinones and 1-alkyl-2(2H)-quinolinones by oxidation with potassium permanganate
Venkov,Statkova-Abeghe
, p. 1451 - 1460 (2007/10/03)
Synthesis of 3,4-dihydroisoquinolines 2, 2-alkyl- 6 and 2-acyl-3,4-dihydro-1(2H)-isoquinolinones 9, 2-alkyl-1(2H)-isoquinolinones 14, N-alkyl-3,4-dihydro-2(2H)-quinolinones 16 and N-alkyl-2(2H)-quinolinones 19 by oxidation of 1,2,3,4-tetrahydroisoquinolines 1, N-alkyl (acyl)iminium salts of 3,4-dihydroisoquinolines 5,8 and isoquinoline 13 as well as of N-alkyl ammonium salts of tetrahydroquinoline 15 and quinoline 18 with potassium permanganate is described.
ISOMERIZING RECYCLIZATION OF QUATERNARY SALTS OF ETHYL 3-(2-PYRIDYL)BUTYRATE AND DIETHYL 2-(2-PYRIDYL)ETHYLMALONATE
Ignatchenko, A. V.,Terent'ev, P. B.
, p. 292 - 295 (2007/10/02)
A number of quaternary salts of ethyl γ-pyridylbutyrate and diethyl β-pyridylethylmalonate undergo the Kost-Sagitullin reaction to give N-methyl-2-quinolone and 3-methylaminocarbamoyl-N-methyl-2-quinolone.Rearrangement in the presence of excess aliphatic amines is accompanied by an efficiently proceeding trans-amination.
