151427-07-5Relevant articles and documents
Copper-Catalyzed Aza-Sonogashira Cross-Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles
Lavernhe, Rémi,Torres-Ochoa, Rubén O.,Wang, Qian,Zhu, Jieping
supporting information, p. 24028 - 24033 (2021/10/07)
Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.
Rh-Catalyzed Conversion of 3-Diazoindolin-2-imines to 5H-Pyrazino[2,3-b]indoles with Photoluminescent Properties
Ding, Hualong,Wang, Zaibin,Bai, Songlin,Lu, Ping,Wang, Yanguang
supporting information, p. 6514 - 6517 (2017/12/26)
A rhodium-catalyzed reaction between 3-diazoindolin-2-imines and 2H-azirines, followed by treatment with a base, furnishes 5H-pyrazino[2,3-b]indoles in excellent yields. A number of functional groups tolerate the reaction conditions, and the resulting 5H-
Practical syntheses of N-acetyl (E)-β-arylenamides
Cai, Zhihua,Liu, Guodu,Jiao, Guangjun,Senanayake, Chris H.,Tang, Wenjun
, p. 3355 - 3360 (2014/01/06)
A facile and practical method for the preparation of (E)-β- arylenamides [(E)-N-(1-arylprop-1-en-2-yl]acetamides] has been developed by reductive acetylation of the corresponding oximes with iron(II) acetate as the reducing reagent. Employment of hexamethylphosphoramide as the solvent was found to be critical for the high E/Z selectivity. The methodology has been applied in efficient syntheses of a key chiral intermediate of tamsulosin by asymmetric hydrogenation. Georg Thieme Verlag Stuttgart . New York.
Synthesis and monoamine transporter binding properties of 2β-[3′-(substituted benzyl)isoxazol-5-yl]- and 2β-[3′-methyl-4′-(substituted phenyl)isoxazol-5-yl]-3β-(substituted phenyl)tropanes
Jin, Chunyang,Navarro, Hernan A.,Page, Kevin,Carroll, F. Ivy
, p. 6682 - 6688 (2008/12/22)
A series of 2β-[3′-(substituted benzyl)isoxazol-5-yl]- and 2β-[3′-methyl-4′-(substituted phenyl)isoxazol-5-yl]-3β-(substituted phenyl)tropanes were prepared and evaluated for affinities at dopamine, serotonin, and norepinephrine transporters using competitive radioligand binding assays. The 2β-[3′-(substituted benzyl)isoxazol-5-yl]-3β-(substituted phenyl)tropanes (3a-h) showed high binding affinities for the dopamine transporter (DAT). The IC50 values ranged from 5.9 to 22 nM. On the other hand, the 2β-[3′-methyl-4′-(substituted phenyl)isoxazol-5-yl]-3β-(substituted phenyl)tropanes (4a-h), with IC50 values ranging from 65 to 173 nM, were approximately 3- to 25-fold less potent than the corresponding 2β-[3′-(substituted benzyl)isoxazol]tropanes. All tested compounds were selective for the DAT relative to the norepinephrine transporter (NET) and serotonin transporter (5-HTT). 3β-(4-Methylphenyl)-2β-[3′-(4-fluorobenzyl)isoxazol-5-yl]tropane (3b) with IC50 of 5.9 nM at the DAT and Kis of 454 and 113 nM at the NET and 5-HTT, respectively, was the most potent and DAT-selective analog. Molecular modeling studies suggested that the rigid conformation of the isoxazole side chain in 4a-h might play an important role on their low DAT binding affinities.
