54537-96-1Relevant academic research and scientific papers
Novel transformation of aryl 2-iodophenyl ketones into 1,3-diarylisoquinolines with (TMS)2NH, styrenes, NIS, and tBuOK
Shibasaki, Kaho,Togo, Hideo
, (2020/12/25)
Treatment of aryl 2-iodophenyl ketones with TMS2NH in the presence of Sc(OTf)3 at warming conditions, followed by the reaction with styrenes and NIS gave N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines. Further treatment of N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines with tBuOK in the presence of 1,10-phenanthroline at 120 °C generated 1,3-diarylisoquinolines in moderate yields through SET from tBuOK onto the iodophenyl group to form aryl radicals, their 6-endo-trig cyclization onto the vinyl groups, and aromatization of the cyclized intermediates. The present method is a novel approach for the preparation of the isoquinoline core via two steps from aryl 2-iodophenyl ketones.
Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution
Li, Quanzhe,Yu, Liuzhu,Wei, Yin,Shi, Min
, p. 9282 - 9296 (2019/08/12)
A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.
Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones via Intramolecular Rearrangement of (E)-3-Styrylquinolin-4(1 H)-ones under Irradiation with 365 nm UV Light
Jing, Sisi,He, Yun,Wang, Tao,Zhang, Jin,Cheng, Anqi,Liang, Yong,Zhang, Zunting
, p. 1578 - 1582 (2018/06/26)
A highly efficient and environmentally friendly synthesis of (2-aminophenyl)(naphthalen-2-yl)methanones was developed. The (2-aminophenyl)(naphthalen-2-yl)methanone derivatives were obtained in high yields (up to 96%) by the irradiation of (E)-3-styrylquinolin-4(1 H)-ones in EtOH-H 2 O (7:1) with UV light (365 nm) at room temperature under Ar atmosphere. The demonstrated photoinduced intramolecular rearrangement has advantages over other transition-metal-catalyzed reactions, e.g. no requirement of additives, green solvent, broad substrate scope, and high atom efficiency.
Reactivity of 2,1-Benzisoxazole in Palladium-Catalyzed Direct Arylation with Aryl Bromides
Aidene, Mohand,Belkessam, Fatma,Soulé, Jean-Fran?ois,Doucet, Henri
, p. 1583 - 1590 (2016/05/02)
The Pd-catalyzed direct arylation of 2,1-benzisoxazole with aryl bromides to access 3-arylbenzoisoxazoles proceeds in moderate-to-high yields with 1 mol % Pd(OAc)2 or 2 mol % PdCl(C3H5)(dppb) (dppb=1,4-bis(diphenylphosphino)butane) as the catalysts and KOAc as an inexpensive base. A wide variety of (hetero)aryl bromides have been employed successfully. Moreover, arylations followed by benzisoxazole ring opening allowed the preparation of 2-aminobenzophenones in only two steps. What a couple: The Pd-catalyzed direct arylation of 2,1-benzisoxazole with aryl bromides and 1 mol % of phosphine-free Pd(OAc)2 catalyst in association with KOAc as an inexpensive base allows the preparation of 3-arylbenzoisoxazoles in moderate-to-high yields. Moreover, the 2,1-benzisoxazole C-3-arylations followed by benzisoxazole ring opening gives access to 2-aminobenzophenones in only two steps.
2-Arylindoles: A new entry to transition metal-free synthesis of 2-aminobenzophenones
Yu, Jin,Moon, Hye Ran,Min, Beom Kyu,Kim, Jae Nyoung
supporting information, p. 893 - 897 (2016/06/14)
Various 2-aminobenzophenones were synthesized from readily available 2-arylindoles in DMSO under O2 balloon atmosphere. The synthesis was carried out without the aid of a transition metal catalyst or moisture-sensitive organometallic reagents from 2-arylindoles.
Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Thota Jagadeshwar,Sridhar, Balasubramanian,Reddy, Maddi Sridhar
supporting information, p. 2226 - 2229 (2015/05/13)
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C - C bond migration. (Chemical Equation Presented).
Palladium-catalyzed direct addition of 2-Aminobenzonitriles to sodium arylsulfinates: Synthesis of o-Aminobenzophenones
Chen, Jiuxi,Li, Jianjun,Su, Weike
, p. 6439 - 6449 (2014/06/10)
The first example of the palladium-catalyzed synthesis of o-Aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-Aminobenzonitriles was reported. A plausible mechanism for the formation of o-Aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-Aminobenzophenones.
Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles
Chen, Jiuxi,Ye, Leping,Su, Weike
supporting information, p. 8204 - 8211 (2015/01/08)
A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is
