349407-89-2Relevant academic research and scientific papers
Efficient Approach to Amide Bond Formation with Nitriles and Peroxides: One-Pot Access to Boronated β-Ketoamides
Gore, Babasaheb Sopan,Senadi, Gopal Chandru,Garkhedkar, Amol Milind,Wang, Jeh-Jeng
, p. 3014 - 3021 (2017)
An efficient, mild and practical approach for the synthesis of amides from nitriles and peroxides is reported in the presence of boron trifluoride ethereate. In this protocol, we utilized peroxides as C1 synthons for the amidation reaction. Als
Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis
Park, Jin,Park, Sehoon,Jang, Gwang Seok,Kim, Ran Hui,Jung, Jaehoon,Woo, Sang Kook
, p. 9995 - 9998 (2021/10/06)
The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.
Identifying Amidyl Radicals for Intermolecular C-H Functionalizations
Tierney, Matthew M.,Crespi, Stefano,Ravelli, Davide,Alexanian, Erik J.
, p. 12983 - 12991 (2019/10/02)
Recent studies have demonstrated the capabilities of amidyl radicals to facilitate a range of intermolecular functionalizations of unactivated, aliphatic C-H bonds. Relatively little information is known regarding the important structural and electronic features of amidyl and related radicals that impart efficient reactivity. Herein, we evaluate a diverse range of nitrogen-centered radicals in unactivated, aliphatic C-H chlorinations. These studies establish the salient features of nitrogen-centered radicals critical to these reactions in order to expedite the future development of new site-selective, intermolecular C-H functionalizations.
A Visible-Light-Driven, Metal-free Route to Aromatic Amides via Radical Arylation of Isonitriles
Malacarne, Marco,Protti, Stefano,Fagnoni, Maurizio
supporting information, p. 3826 - 3830 (2017/11/15)
The photochemical metal-free carboamidation of aryl radicals has been exploited for the preparation of aromatic amides, including hetero- and polyaromatic derivatives, under visible light irradiation of arylazo sulfones in the presence of isocyanides in aqueous acetonitrile. The process was useful for the smooth preparation of the antidepressant moclobemide. (Figure presented.).
Bu4NI-Catalyzed Oxygen-Centered Radical Addition between Acyl Peroxides and Isocyanides
Chen, Meng,Li, Yang,Tang, Hong,Ding, Hao,Wang, Kai,Yang, Lingen,Li, Cuiting,Gao, Meng,Lei, Aiwen
supporting information, p. 3147 - 3150 (2017/06/23)
A novel oxygen-centered radical addition between acyl peroxides and isocyanides has been developed. A diverse collection of valuable arylcarboxyamides were easily synthesized by this protocol. From the preliminary mechanistic study, the elimination of carbon dioxide affords the product via an intramolecular rearrangement.
Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon
Liu, Zhiqiang,Zhang, Xinglu,Li, Jian,Li, Jianxiong,Li, Feng,Li, Chunju,Jia, Xueshun
, p. 4052 - 4055 (2016/08/30)
An unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst is disclosed. The experimental results and mechanistic study show that the isocyano group acts formally as an N1 synthon during the transformation, thus expanding the reactivity profile of isocyanide.
Substituent effects in aminocarbonylation of para-substituted iodobenzenes
Marosv?lgyi-Haskó, Diána,Kégl, Tamás,Kollár, László
supporting information, p. 7509 - 7516 (2016/11/11)
Iodobenzene derivatives possessing various substituents (amino, hydroxy, tert-butyl, methyl, isopropyl, phenyl, fluoro, chloro, methoxycarbonyl, acetyl, trifluoromethyl, nitro) in the para position were aminocarbonylated using tert-butylamine and n-butylamine as N-nucleophiles. A palladium(0) catalyst formed in situ from palladium(II) acetate and triphenylphosphine was used. Carboxamide and ketocarboxamide type compounds were formed via single and double carbon monoxide insertion, respectively. While 4-substituents with negative Hammett constants (σp) decrease reactivity of the substrates, the iodoaromatics possessing electron-withdrawing group (characterized by positive Hammett constants (σp)) in the 4-position have shown high reactivity. Highly active catalysts were obtained in the presence of xantphos accompanied by the chemoselective formation of the corresponding carboxamides. The difference in reactivity of iodoarene and bromoarene functionalities enabled the synthesis of bromo-substituted compounds suitable for further functionalization.
INHIBITORS OF BRUTON'S TYROSINE KINASE
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Page/Page column 44, (2014/04/03)
This application discloses compounds according to generic Formula I: wherein all variables are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation such as rheumatoid arthritis. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.
Synthesis of amides via palladium-catalyzed amidation of aryl halides
Jiang, Huanfeng,Liu, Bifu,Li, Yibiao,Wang, Azhong,Huang, Huawen
supporting information; experimental part, p. 1028 - 1031 (2011/04/27)
A new and efficient method for the synthesis of amides via palladium-catalyzed C-C coupling of aryl halides with isocyanides is reported, by which a series of amides were formed from readily available starting materials under mild conditions. This transformation could extend its use to the synthesis of natural products and significant pharmaceuticals.(Figure Presented)
