26862-65-7Relevant academic research and scientific papers
Selective Thiocyanation and Aromatic Amination to Achieve Organized Annulation of Enaminone with Thiocyanate
Feng, Xukai,Leng, Xin,Li, Jianli,Li, Yao,Liu, Hua,Liu, Lang,Liu, Ping,She, Mengyao,Zhang, Jun,Zhang, Shengyong,Zheng, Tingting
, p. 8396 - 8401 (2021/11/17)
A tandem insertion of thiocyanate to enamine was performed for the regioselective synthesis of multisubstituted benzoimidazo[2,1-b]thiazoles. This method was shown to be effective in addressing the issue of isomerization encountered in common strategies. With a change made to the leading group on the aniline fragment of enamine, the reaction achieved different transformations, thus enabling multisubstituted benzo[4,5]imidazo[2,1-b]thiazoles and thiazoles in satisfactory yields.
Regio-and stereoselective C(sp2)-H acylation of enamides with aldehydes: Via transition-metal-free photoredox catalysis
Li, Wei-Ming,Loh, Teck-Peng,Tao, Ji-Yu,Wu, Jia-Xu,Wu, Xian-Dan,Zhang, Xiao-Chen,Zhao, Kai,Zhu, Tong-Hao
supporting information, p. 5497 - 5503 (2020/09/17)
A straightforward and efficient C(sp2)-H acylation of enamides with aldehydes via transition-metal-free photoredox catalysis is demonstrated. The transformation proceeded smoothly without resorting to expensive and potentially toxic iridium or ruthenium polypyridyl-based photocatalysts under mild conditions, furnishing a diverse range of synthetically crucial, geometrically defined β-acylated enamides in a stereoselective and regioselective manner. This journal is
Palladium-catalyzed cyclization reaction of N-(2-Haloaryl)alkynylimines: Synthesis of 3-acylindoles using water as the sole solvent and oxygen source
Zhang, An-An,Meng, Tuanjie,Wang, Wenli,Liu, Xueli,Zhu, Yupei,Liu, Lantao
, (2020/02/04)
A simple and efficient strategy for the preparation of 3-acylindoles via palladium-catalyzed cyclization reaction of N-(2-haloaryl)alkynylimines in water has been developed. The reaction tolerates a wide range of functional groups, and the corresponding 3-acylindoles were obtained in high yields using water as the sole solvent and oxygen sources. Additionally, this method could provide a short synthesis route for Pravadoline, a phase II analgesic drug.
A competitive and highly selective 7-, 6- And 5-annulation with 1,3-migration through C-H and N-H-alkyne coupling
Ajarul, Sk,Kayet, Anirban,Pati, Tanmay K.,Maiti, Dilip K.
supporting information, p. 474 - 477 (2020/01/13)
We demonstrated a highly competitive and selective C-C and N-C cross-coupled 7-, 6- and 5-annulation utilizing 2-ethynylanilides to afford functionalized 1H-benzo[b]azepin-2(5H)-ones, 2-quinolinones, and 3-acylindoles in high yield. ZnCl2 was f
Copper-promoted Chan-Lam coupling between enaminones and aryl boronic acids
Duan, Xiyan,Liu, Ning,Liu, Kun,Song, Yakun,Wang, Jia,Mao, Xianhua,Xu, Weidong,Yang, Shijie,Li, Huixian,Ma, Junying
supporting information, p. 4187 - 4190 (2018/10/24)
A novel copper-promoted N-arylation of enaminones with aromatic boronic acids has been developed, which provides an efficient way to synthesize N-aryl enaminones with a broad substrate scope and excellent functional group compatibility. The N-aryl enaminones could be converted into a series of highly valuable building blocks and bioactive compounds. Notably, in comparison with traditional methods, this alternative approach provides accesses to N-aryl enaminones bearing multiple aromatic rings.
Direct synthesis of 3-acylbenzothiophenes: Via the radical cyclization of 2-alkynylthioanisoles with α-oxocarboxylic acids
Liu, Wei,Hu, Yao-Qian,Hong, Xiao-Yi,Li, Guo-Xing,Huang, Xiao-Bo,Gao, Wen-Xia,Liu, Miao-Chang,Xia, Yuanzhi,Zhou, Yun-Bing,Wu, Hua-Yue
supporting information, p. 14148 - 14151 (2019/01/03)
A radical cascade cyclization of 2-alkynylthioanisoles with α-oxocarboxylic acids with AgNO3 has been described. This reaction provides a novel route to directly access 3-acylbenzothiophenes from simple chemical feedstocks. In particular, the utility of the approach was demonstrated by its application to the synthesis of a polymerization inhibitor and a raloxifene precursor.
Direct Synthesis of 3-Acylindoles through Rhodium(III)-Catalyzed Annulation of N-Phenylamidines with α-Cl Ketones
Zhou, Jianhui,Li, Jian,Li, Yazhou,Wu, Chenglin,He, Guoxue,Yang, Qiaolan,Zhou, Yu,Liu, Hong
supporting information, p. 7645 - 7649 (2018/12/11)
In the present study, a novel synthetic strategy to directly produce versatile 3-acylindoles through Rh(III)-catalyzed C-H activation and annulation cascade of N-phenylamidines with α-Cl ketones was developed, in which α-Cl ketones serve as unusual one-carbon (sp3) synthons. This strategy features high regioselectivity, efficiency, wide substrate tolerance, and mild reaction conditions, which further underscore its synthetic utility in drug molecule synthesis.
Electrocatalytic intramolecular oxidative annulation of: N -aryl enamines into substituted indoles mediated by iodides
Tang, Shan,Gao, Xinlong,Lei, Aiwen
supporting information, p. 3354 - 3356 (2017/03/22)
An electrocatalytic reaction protocol is developed for achieving intramolecular dehydrogenative annulation of N-aryl enamines. It offers a simple and efficient way for the synthesis of indoles in an undivided cell. Good to excellent yields are obtained un
Iodine/Copper Iodide-Mediated C-H Functionalization: Synthesis of Imidazo[1,2-a]pyridines and Indoles from N-Aryl Enamines
Liu, Jing,Wei, Wei,Zhao, Ting,Liu, Xuanyu,Wu, Jie,Yu, Wenquan,Chang, Junbiao
, p. 9326 - 9336 (2016/10/14)
A practical intramolecular C-H functionalization reaction of N-aryl enamines has been carried out with molecular iodine (I2) as the sole oxidant in the presence of copper iodide (CuI). The efficient and versatile synthetic method described here
Decarboxylative/decarbonylative C3-acylation of indoles: Via photocatalysis: A simple and efficient route to 3-acylindoles
Shi, Qing,Li, Pinhua,Zhu, Xianjin,Wang, Lei
, p. 4916 - 4923 (2016/11/04)
A simple and efficient strategy for the preparation of 3-acylindoles via visible-light promoted C3-acylation of free (NH)- and N-substituted indoles with α-oxocarboxylic acids was developed. The reaction tolerates a wide range of functional groups, and the corresponding 3-acylindoles were obtained in high yields under mild conditions.
