92962-52-2Relevant academic research and scientific papers
Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2-Substituted Indole-3-glyoxylates
Vidyasagar, Adiyala,Shi, Jinwei,Kreitmeier, Peter,Reiser, Oliver
, (2018/11/23)
A visible-light-mediated radical tandem cyclization of ortho-isocyano-α-bromo cinnamates to 2-substituted indole-3-glyoxylates is achieved by formation of both C-C/C-S and C-O bonds. The reaction proceeds through a hitherto unprecedented bromine- or metho
Tandem cyclisation of vinyl radicals: A sustainable approach to indolines utilizing visible-light photoredox catalysis
Pagire, Santosh K.,Reiser, Oliver
, p. 1721 - 1725 (2017/06/07)
A tin-free method for the synthesis of substituted indolines has been developed generating vinyl radicals by visible-light-promoted photocatalysis in a reductive quenching cycle. This strategy offers a mild, robust, and high yielding pathway to a wide range of indolines containing diverse electronic substituents. The so obtained 2,3-disubstituted indolines serve as valuable precursors for the synthesis of biologically active molecules, which is demonstrated with the formal synthesis of tryptamines and furoindolines.
N-Heterocyclic-Carbene-Catalyzed Umpolung of Imines
Patra, Atanu,Mukherjee, Subrata,Das, Tamal Kanti,Jain, Shailja,Gonnade, Rajesh G.,Biju, Akkattu T.
, p. 2730 - 2734 (2017/02/26)
N-Heterocyclic carbene (NHC) catalysis has been widely used for the umpolung of aldehydes, and recently for the umpolung of Michael acceptors. Described herein is the umpolung of aldimines catalyzed by NHCs, and the reaction likely proceeds via aza-Breslo
An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives
Xu, Jun,Tong, Rongbiao
, p. 2952 - 2956 (2017/07/24)
An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.
Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells
Sherer, Christopher,Tolaymat, Ibrahim,Rowther, Farzana,Warr, Tracy,Snape, Timothy J.
, p. 1561 - 1565 (2017/03/16)
The prognosis for glioblastoma patients is, at best, poor, with the median time of survival after diagnosis measured in months. As such, there is much need for the rapid development of potent and novel treatments. Herein, we report our preliminary findings on the SAR of a series of indole-3-carbinol and related fragments and reveal a potent lead with low micromolar activity against a particularly resistant glioblastoma cell culture, providing a new platform for future development of a new therapy in this area.
Rhodium(III)-catalyzed c-h activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group
Zheng, Liyao,Hua, Ruimao
supporting information, p. 2352 - 2356 (2014/03/21)
An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for RhIII-catalyzed C-H activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and Ci￡O source, whereas its N-N bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DGauto). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DGauto strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated. Copyright
Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade
Han, Long,Liu, Chuan,Zhang, Wei,Shi, Xiao-Xin,You, Shu-Li
, p. 1231 - 1233 (2014/02/14)
An enantioselective epoxidation of tryptophols followed by an intramolecular epoxide opening reaction was realized by chiral vanadium catalysts derived from C2 symmetric bis-hydroxamic acid (BHA) ligands. 3a-Hydroxyfuroindoline derivatives with up to 89% yield and 90% ee were obtained under mild reaction conditions.
Copper(I)-catalyzed cascade dearomatization of 2-substituted tryptophols with arylidonium salts
Liu, Chuan,Zhang, Wei,Dai, Li-Xin,You, Shu-Li
, p. 4525 - 4527 (2012/10/29)
Copper(I)-catalyzed dearomative arylation and vinylation of 2-substituted tryptophols were realized with a subsequent cyclization reaction. The cascade dearomatization sequence provided versatile furoindoline derivatives with two quaternary carbon centers
