255724-68-6Relevant articles and documents
Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines
Zhang, Zi-Qi,Xu, Yi-Hao,Dai, Jing-Cheng,Li, Yan,Sheng, Jie,Wang, Xi-Sheng
, p. 2194 - 2198 (2021/04/05)
A facile and efficient approach for the synthesis of the CF3-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method has demonstrated low cataly
Photoinduced Radical Cascade Cyclization: A Metal-Free Approach to Access Difluoroalkylated Dioxodibenzothiazepines
Deng, Yinglan,Jian, Jing-Xin,Lu, Maojian,Tong, Qing-Xiao,Xiao, Qian,Zhong, Jian-Ji
, p. 9303 - 9308 (2021/12/06)
A simple and mild photoredox catalytic approach to access difluoroalkylated dioxodibenzothiazepines in high regioselectivity via radical cascade cyclization has been described herein. In contrast to previous methods, this strategy does not involve the use
Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines
Du, Li-Juan,Han, Ya-Ping,Liang, Yong-Min,Zhang, Hong-Yu,Zhang, Yuecheng,Zhao, Jiquan
, (2020/03/04)
A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.
Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems
He, Min,Chen, Nuan,Zhou, Ting,Li, Qing,Li, Hongguang,Lang, Ming,Wang, Jian,Peng, Shiyong
, p. 9559 - 9563 (2019/11/21)
An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.
Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines
Ye, Yibin,Cheung, Kelvin Pak Shing,He, Lisi,Tsui, Gavin Chit
supporting information, p. 1676 - 1679 (2018/03/23)
A new method for the synthesis of 2-(trifluoromethyl)indoles using easily accessible 2-alkynylanilines and a well-established fluoroform-derived CuCF3 reagent is described. This method utilizes a domino trifluoromethylation/cyclization strategy
Cs2CO3 as a source of carbonyl and ethereal oxygen in a Cu-catalysed cascade synthesis of benzofuran [3,2-: C] quinolin-6[5- H] ones
Ali, Wajid,Modi, Anju,Behera, Ahalya,Mohanta, Prakash Ranjan,Patel, Bhisma K.
, p. 5940 - 5944 (2016/07/06)
The simultaneous construction of C-C, C-O, and C-N bonds utilizing Cs2CO3 as a source of both carbonyl (CO) and ethereal oxygen and a cascade synthesis of benzofuro[3,2-c]quinolin-6(5H)-one have been achieved using a combination of C
Pd/C-catalyzed cyclizative cross-coupling of two ortho-alkynylanilines under aerobic conditions: Synthesis of 2,3′-bisindoles
Yao, Bo,Wang, Qian,Zhu, Jieping
supporting information, p. 7413 - 7416 (2015/05/13)
Abstract A palladium-catalyzed cyclizative cross-coupling of two o-alkynylanilines to 2,3′-bisindoles under aerobic oxidative conditions was developed. Mechanistic studies suggested that the two catalytic cycles, namely the formation of 3-alkynylindoles 8
3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT2A receptor antagonists
Rowley,Hallett,Goodacre,Moyes,Crawforth,Sparey,Patel,Marwood,Patel,Thomas,Hitzel,O'Connor,Szeto,Castro,Hutson,Macleod
, p. 1603 - 1614 (2007/10/03)
The development of very high affinity, selective, and bioavailable h5-HT2A receptor antagonists is described. By investigation of the optimal position for the basic nitrogen in a series of 2-phenyl-3-piperidylindoles, it was found that with the basic nitrogen at the 3-position of the piperidine it was not necessary to further substitute the piperidine in order to obtain good binding at h5-HT2A receptors. This meant the compounds no longer had high affinity at the IKr potassium channel, an issue with previous series of 2-aryl-3-(4-piperidyl)indoles. Improvements could be made to oral bioavailability in this series by reduction of the pKa of the basic nitrogen, by adding a fluorine atom to the piperidine ring, leading to 3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (17). Metabolic studies with this compound identified oxidation at the 6-position of the indole as a major route in vitro and in vivo in rats. Blocking this position with a fluorine atom led to 6-fluoro-3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (22), an antagonist with 0.06 nM affinity for h5-HT2A receptors, with bioavailability of 80% and half-life of 12 h in rats.
