1217-80-7Relevant academic research and scientific papers
Pd(II)-Catalyzed Intramolecular C(sp2)-H Arylation of Tryptamines Using the Nonsteric NH2as a Directing Group
Wang, Sixi,Yu, Bin,Liu, Hong-Min
supporting information, p. 42 - 48 (2021/01/09)
The free amine-directed C-H functionalization reactions are challenging and mainly restricted to bulky amines. In this work, we report the nonsteric NH2-directed Pd(II)-catalyzed intramolecular C(sp2)-H arylation of tryptamines, which enables the efficient, gram-scale, and regioselective synthesis of versatile 2-aryltryptamines (35 examples, up to 98% yield). This approach broadens the substrate scope of the free amine-directed C-H functionalization, not limited to bulky amine substrates. Late-stage elaborations of 2-aryltryptamines achieve the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as aurantioclavine, chimonanthine, and phalarine.
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.
Access to 2-Arylindoles via Decarboxylative C?C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts
Arun, Velladurai,Pilania, Meenakshi,Kumar, Dalip
supporting information, p. 3345 - 3349 (2016/12/14)
Easily accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2-arylindoles and heteroaryl carboxylates in a regioselective fashion. C2-arylated indoles were produced using a Pd-catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base-free conditions. This protocol was successfully utilized to synthesize Paullone, a cyclin-dependent kinase (CDK) inhibitor.
Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-Type cascade to construct polycyclic spiroindolines
Zhao, Xiaohu,Liu, Xiaohua,Mei, Hongjiang,Guo, Jing,Lin, Lili,Feng, Xiaoming
supporting information, p. 4032 - 4035 (2015/03/30)
A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N-dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction.
Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate
Montgomery, Thomas D.,Nibbs, Antoinette E.,Zhu, Ye,Rawal, Viresh H.
, p. 3480 - 3483 (2014/07/21)
We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.
Synthesis of C-2 arylated tryptophan amino acids and related compounds through palladium-catalyzed C-H Activation
Preciado, Sara,Mendive-Tapia, Lorena,Albericio, Fernando,Lavilla, Rodolfo
, p. 8129 - 8135 (2013/09/12)
Tryptophan (Trp) and tryptophan derivatives are C2-arylated. A C-H activation process allows the preparation of both protected and unprotected arylated-Trp amino acids, directly from the amino acid precursor and aryl iodides. The obtained compounds are suitable for standard solid-phase peptide synthesis.
3-Substituted 2-phenyl-indoles: Privileged structures for medicinal chemistry
Johansson, Henrik,Jorgensen, Tanja Bogeloov,Gloriam, David E.,Braeuner-Osborne, Hans,Pedersen, Daniel Sejer
, p. 945 - 960 (2013/04/24)
Privileged structures have been used in drug discovery targeting G protein-coupled receptors (GPCR) and other protein classes for more than 20 years. Their rich activity profiles and drug-like characteristics lend themselves to increased productivity in hit identification and lead optimisation. Recently we discovered two allosteric modulators 1 and 2 for the G protein-coupled receptor GPRC6A incorporating the privileged 2-phenyl-indole scaffold, functionalised at the 3-position. In order to develop new potential GPRC6A ligands we engaged in the development of synthetic routes to provide 2-phenyl-indoles with a variety of substituents at the indole 3-position. Herein we describe the development of optimised and efficient synthetic routes to a series of new 2-phenyl-indole building blocks 3 to 9 and show that these can be used to generate a broad variety of 3-substituted 2-phenyl-indoles of interest to medicinal chemists.
Intercepting bacterial indole signaling with flustramine derivatives
Bunders, Cynthia A.,Minvielle, Marine J.,Worthington, Roberta J.,Ortiz, Minoshka,Cavanagh, John,Melander, Christian
supporting information; scheme or table, p. 20160 - 20163 (2012/01/15)
Indole signaling is one of the putative universal signaling networks in bacteria. We have investigated the use of desformylflustrabromine (dFBr) derivatives for the inhibition of biofilm formation through modulation of the indole-signaling network in Escherichia coli and Staphylococcus aureus. We have found dFBr derivatives that are 10-1000 times more active than indole itself, demonstrating that the flustramine family of indolic natural products represent a privileged scaffold for the design of molecules to control pathogenic bacterial behavior.
Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase
Weinstein, David S.,Liu, Wen,Gu, Zhengxiang,Langevine, Charles,Ngu, Khehyong,Fadnis, Leena,Combs, Donald W.,Sitkoff, Doree,Ahmad, Saleem,Zhuang, Shaobin,Chen, Xing,Wang, Feng-Lai,Loughney, Deborah A.,Atwal, Karnail S.,Zahler, Robert,Macor, John E.,Madsen, Cort S.,Murugesan, Natesan
, p. 1435 - 1440 (2007/10/03)
A series of inhibitors of mammalian 15-lipoxygenase based on tryptamine and homotryptamine scaffolds is described. Compounds with aryl substituents at C-2 of the indole core of tryptamine and homotryptamine sulfonamides (e.g., 37a-p) proved to be potent i
A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and β-carbolines
Wu, Tom Y. H.,Schulte, Peter G.
, p. 4033 - 4035 (2007/10/03)
(matrix presented) Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. β-Carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R1. Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R2. If X = Br, Suzuki coupling can be used to introduce R3. After derivatization, the indole derivatives are activated with methyl iodide and released under mild basic condition.
