38348-83-3Relevant articles and documents
Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles: Via the ring contraction and deformylative functionalization of piperidine derivatives
Wang, Fang,Zhang, Xinying,He, Yan,Fan, Xuesen
, p. 156 - 164 (2019/01/08)
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.
Aluminium Chloride-Mediated Synthesis of 1-Chloro-2,2,2-Trifluoroethylidene-Substituted Pyrrolidones
Wang, Zeng,Yuan, Zihang,Han, Xiaoyan,Weng, Zhiqiang
supporting information, p. 2178 - 2182 (2018/04/25)
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.).
Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water
Tan, Bryan Yong-Hao,Teo, Yong-Chua
supporting information, p. 1697 - 1701 (2015/07/20)
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.
