- Ruthenium-catalyzed synthesis of: N -substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines
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Herein, we report the first example of synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step, which was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene-phosphine-phosphine ligand as the catalyst.
- Zheng, Yanling,Nie, Xufeng,Long, Yang,Ji, Li,Fu, Haiyan,Zheng, Xueli,Chen, Hua,Li, Ruixiang
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supporting information
p. 12384 - 12387
(2019/10/19)
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- Aluminium Chloride-Mediated Synthesis of 1-Chloro-2,2,2-Trifluoroethylidene-Substituted Pyrrolidones
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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
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supporting information
p. 2178 - 2182
(2018/04/25)
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- Synthesis of N -Aryl and N -Heteroaryl γ-, δ-, and ?-Lactams Using Deprotometalation-Iodination and N -Arylation, and Properties Thereof
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Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl 2 ·TMEDA (M = Zn or Cd; TMEDA = N, N, N ′, N ′-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N -arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using dimethyl sulfoxide as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.
- Amara, Rim,Bentabed-Ababsa, Ghenia,Hedidi, Madani,Khoury, Joseph,Awad, Ha?an,Nassar, Ekhlass,Roisnel, Thierry,Dorcet, Vincent,Chevallier, Floris,Fajloun, Ziad,Mongin, Florence
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p. 4500 - 4516
(2017/09/26)
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- Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water
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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
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supporting information
p. 1697 - 1701
(2015/07/20)
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- Palladium-catalyzed coupling of lactams with bromobenzenes
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An efficient method for the coupling of lactams with bromobenzenes mediated by palladium acetate and DPPF is presented. The reaction proceeds efficiency with a variety of lactams and both electron-rich and poor substituted bromobenzenes.
- Shakespeare, William C.
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p. 2035 - 2038
(2007/10/03)
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- 7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridines as novel inhibitors of human eosinophil phosphodiesterase
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High-throughput file screening against inhibition of human lung PDE4 led to the discovery of 3-ethyl-1-(4-fluorophenyl)-6-phenyl-7-oxo-4,5,6,7,- tetrahydro-1H-pyrazolo[3,4-c]pyridine (11) as a novel PDE4 inhibitor. Subsequent SAR development, using an eosinophil PDE assay, led to analogues up to 50-fold more potent than 11 with IC50 values of 0.03-1.6 μM. One such compound, CP-220,629 (22) (IC50 = 0.44 μM), was efficacious in the guinea pig aerosolized antigen induced airway obstruction assay (ED50 2.0 mg/kg, po) and demonstrated a significant reduction in eosinophil (55%), neutrophil (65%), and IL-1β (82%) responses to antigen challenge in atopic monkeys (10 mg/kg, po).
- Duplantier, Allen J.,Andresen, Catharine J.,Cheng, John B.,Cohan, Victoria L.,Decker, Christian,DiCapua, Frank M.,Kraus, Kenneth G.,Johnson, Kerry L.,Turner, Claudia R.,UmLand, John P.,Watson, John W.,Wester, Ronald T.,Williams, Alison S.,Williams, John A.
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p. 2268 - 2277
(2007/10/03)
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