928782-97-2Relevant academic research and scientific papers
Cascade Reactions Assisted by Microwave Irradiation: Ultrafast Construction of 2-Quinolinone-Fused γ-Lactones fromN-(o-Ethynylaryl)acrylamides and Formamide
Sacchelli, Bruce A. L.,Rocha, Bianca C.,Andrade, Leandro H.
, p. 5071 - 5075 (2021/07/20)
An ultrafast (10 s) methodology to construct novel highly functionalized 2-quinolinones fromN-(o-ethynylaryl)acrylamides (1,7-enynes) is described for the first time. Microwave irradiation enabled the ultrafast synthesis of 2-quinolinone-fused γ-lactones from Fenton’s reagents in formamide. After six key consecutive reactions, including a diastereoselective step, 2-quinolinone-fused γ-lactones were obtained in good overall yield (up to 46%; 10 s).
Regioselective Synthesis of Substituted Carbazoles, Bicarbazoles, and Clausine C
Points, Gary L.,Beaudry, Christopher M.
supporting information, p. 6882 - 6885 (2021/09/11)
Substituted carbazoles are efficiently constructed from 3-triflato-2-pyrones and alkynyl anilines. Multiple substituents are tolerated on the carbazole, and complete control of regiochemistry is observed. Complicated and sterically congested substitution patterns are produced. This strategy is also used to prepare substituted bicarbazoles and related biaryls. Finally, the method was showcased in a synthesis of the carbazole natural product clausine C.
Copper(I)-Mediated Cascade Annulation via Dual C-H/C-H Activation: Access to Benzo[a]carbazolic AEEgens
Khandelia, Tamanna,Ghosh, Subhendu,Panigrahi, Pritishree,Shome, Rajib,Ghosh, Siddhartha Sankar,Patel, Bhisma K.
, p. 16948 - 16964 (2021/12/02)
A Cu(I)-mediated cascade cyclization/annulation of unprotectedo-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C-N and two C-C bonds to deliver fused benzo[a]carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485-502 nm with a large Stokes shift and fluorescence lifetime of ～17 ns. The annulated3aadisplays AEE behavior in the ethanol/hexane system and possesses marigold-flower-like morphology at the aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular fluorescence depicts cell imaging applicability.
Catalytic Enantioselective Aminopalladation–Heck Cascade
He, Yu-Ping,Cao, Jian,Wu, Hua,Wang, Qian,Zhu, Jieping
supporting information, p. 7093 - 7097 (2021/02/26)
Domino processes initiated by intramolecular nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains
An expedient route to tricyanovinylindoles and indolylmaleimides fromo-alkynylanilines utilising DMSO as a one-carbon synthon
Chakraborty, Nikita,Dahiya, Anjali,Modi, Anju,Patel, Bhisma K.,Rakshit, Amitava
, p. 6847 - 6857 (2021/08/20)
A Pd(ii)/Cu(ii) catalysed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a one-carbon synthon. The reaction proceedsviathe construction of 2-aryl-3-formyl indole followed by sequential addition of malononitrile and a CN resulting
Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents
Liang, Hao,Zhu, Guoxun,Pu, Xiaoyun,Qiu, Liqin
, p. 9246 - 9250 (2021/12/06)
The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de
Nickel-Catalyzed Arylative Additions on 2-Alkynyl-N-Arylsulfonylanilides to Construct Functionalized Indoles
Dake, Gregory R.,Voth, Christopher N.
supporting information, p. 744 - 748 (2020/02/13)
The addition of aryl iodides to 2-alkynyl-N-sulfonylanilides to form 2,3-difunctionalized N-arylsulfonylindoles can be catalyzed using a nickel catalyst ligated to a bis(cyclohexanyl)phosphinoferrocene. A variety of nickel complexes can be used as precata
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
Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides
Yuan, Shuo,Zhang, Dan-Qing,Zhang, Jing-Ya,Yu, Bin,Liu, Hong-Min
supporting information, p. 814 - 817 (2020/02/04)
Indole and phthalide are privileged heterocyclic scaffolds in numerous natural products and bioactive molecules. The synthesis and biological evaluation of the compounds combining these two scaffolds have rarely been reported. Herein, we repot the first palladium-catalyzed ligand-free double cyclization reactions that enable efficient synthesis of 3-(1′-indolyl)-phthalides (42 examples, up to 96% yield) under mild conditions. Notably, only 1.0 mol % of catalyst loading is used, suggesting high efficiency. Late-stage elaborations give highly functionalized analogues.
Syntheses of N-Alkyl 2-Arylindoles from Saturated Ketones and 2-Arylethynylanilines via Cu-Catalyzed Sequential Dehydrogenation/Aza-Michael Addition/Annulation Cascade
Chen, Linlin,Ling, Fei,Liu, Tao,Ma, Yan,Song, Dingguo,Xiao, Lian,Xu, Min,Yu, Mengyao,Zhong, Weihui
, p. 3224 - 3233 (2020/03/23)
We describe here a Cu-catalyzed and 4-OH-TEMPO-mediated sequential dehydrogenation/aza-Michael addition/annulation cascade reaction for the construction of N-alkyl 2-arylindoles from facilely available saturated ketones and 2-arylethynylanilines. This rea
