- Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles: Via the ring contraction and deformylative functionalization of piperidine derivatives
-
In this paper, a selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the cascade reactions of N-substituted piperidines is presented. Mechanistically, the formation of pyrrolidin-2-ones involves a domino process including the in situ formation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation and ipso-oxidation. On the other hand, 3-iodopyrroles are believed to be formed via the initial generation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation, dehydrogenation, iodination and aromatization. Interestingly, either pyrrolidin-2-ones or 3-iodopyrroles could be obtained selectively from the same substrates, and the selectivity was easily tuned by using a specific oxidant and additive.
- Wang, Fang,Zhang, Xinying,He, Yan,Fan, Xuesen
-
p. 156 - 164
(2019/01/08)
-
- Pyrrolidone compound synthesis method
-
The invention discloses a pyrrolidone compound synthesis method, and belongs to the technical field of organic synthesis. Saturated cyclic tertiary amine 1 is added into solvents, and heating reactionis performed in the presence of oxidizing agent, cupric salt, potassium hydrogen persulfate compound salt (Oxone) and oxygen mixture, additives, elementary iodine or iodated metal salt and the like to obtain pyrrolidone 2. According to the method, a pyrrolidone compound is synthesized by cascade reaction of oxidization retraction, decarbonylation and in-situ oxidization of saturated cyclic tertiary amine compounds, the method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like, and an economical, practical, green and environment-friendly novel method is provided for synthesis of the pyrrolidone compound.
- -
-
Paragraph 0066-0068
(2019/03/08)
-
- Aluminium Chloride-Mediated Synthesis of 1-Chloro-2,2,2-Trifluoroethylidene-Substituted Pyrrolidones
-
An aluminium chloride-mediated cascade reaction between pyrrolidones and trifluoroacetic anhydride is reported. Functionally diverse 1-chloro-2,2,2-trifluoroethylidene-substituted pyrrolidones were obtained in moderate to high yields through electrophilic trifluoroacetylation, nucleophilic chlorination, and elimination. This procedure has a wide scope, good functional-group tolerance and the reaction conditions are amenable to scale up. Additionally the obtained 1-chloro-2,2,2-trifluoroethylidene products can be applied to further functionalization as trifluoromethyl-containing building blocks. Some of the title compounds showed fungicidal activity against cucumber downy mildew (CDM). (Figure presented.).
- Wang, Zeng,Yuan, Zihang,Han, Xiaoyan,Weng, Zhiqiang
-
supporting information
p. 2178 - 2182
(2018/04/25)
-
- INDOLE CARBOXAMIDE COMPOUNDS
-
Disclosed are compounds of Formula (I): or a salt thereof, wherein: X is CR4 or N; R1, R2, R3, R4, and A are defined herein. Also disclosed are methods of using such compounds as inhibitors of Bruton's tyrosine kinase (Btk), and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.
- -
-
Paragraph 0485-0486
(2016/05/19)
-
- Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water
-
A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C2O4)·2H2O/N,N′-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua
-
supporting information
p. 1697 - 1701
(2015/07/20)
-
- Selective copper-catalyzed N-arylation of lactams with arylboronic acids under base- and ligand-free conditions
-
An oxidative copper-catalyzed cross-coupling of arylboronic acids with various ring-size lactams has been developed. The N-arylated lactams were obtained in moderate to excellent yields without any additional bases, ligands, or additives. This reaction shows complete selectivity for N-arylation of lactams in the presence of a hydroxyl group.
- Bathini, Thulasiram,Rawat, Vikas Singh,Sreedhar, Bojja
-
supporting information
p. 1348 - 1351
(2015/06/16)
-
- Heterogeneous CuII-catalysed solvent-controlled selective N-arylation of cyclic amides and amines with bromo-iodoarenes
-
A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalysed by CuII/Al2O3 has been achieved. This protocol has been employed for the synthesis of a library of arenes bearing a cyclic amide and an amine moiety at two ends, including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed electron paramagnetic resonance (EPR) spectroscopy, X-ray photoelectron spectroscopy (XPS), UV diffuse reflectance spectroscopy (DRS) and inductively coupled plasma-mass spectrometry (ICP-MS) studies of the catalyst at different stages of the reaction. The CuII/Al2O 3 catalyst was recovered and recycled for subsequent reactions. One over the other: A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalyzed by CuII/Al2O3 has been achieved (see scheme). This protocol has been employed for the synthesis of a library of arenes bearing cyclic amide and amine moieties at two ends including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed spectroscopic studies (FG=functional group). Copyright
- Kundu, Debasish,Bhadra, Sukalyan,Mukherjee, Nirmalya,Sreedhar, Bojja,Ranu, Brindaban C.
-
p. 15759 - 15768
(2013/11/19)
-
- NOVEL COMPOUNDS
-
The present invention relates to novel NADPH oxidase II inhibitors and their use in the treatment of diseases mediated by the NADPH oxidase enzymes.
- -
-
Page/Page column 60
(2013/02/27)
-
- NOVEL COMPOUNDS
-
The invention provides novel hydantoin derivatives; processes for their preparation; pharmaceutical compositions containing them; a process for preparing the pharmaceutical compositions; and their use in therapy.
- -
-
Page/Page column 41-42
(2009/03/07)
-