17901-58-5Relevant academic research and scientific papers
Electrochemical behavior of indoles with methyl, benzyl, and dibenzyl-4-yl groups
Buder,Schwitzgebel,Samsoniya,Gogritchiani,Chikvaidze
, p. 1121 - 1129 (2005)
2,3-Dimethylindole, N-benzyl-2-methylindole, and 2-(dibenzyl-4-yl)-7- benzylindole (DBBI) under conditions for potentiodynamic electrochemical polymerization (0.3-0.9 V vs. Ag/Ag+ in acetonitrile) underwent dimerization reactions as was shown b
Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor
Abdelli, Abderrahmen,Efrit, Mohamed Lotfi,El-Marrouki, Dalel,Gros, Philippe C.,M’Rabet, Hédi,Touchet, Sabrina
supporting information, p. 1722 - 1731 (2021/06/25)
A convergent strategy is reported for the construction of nitrogen-containing heterocycles from common substrates: 1,4-diketones and primary amines. Indeed, by just varying the substrates, the substituents, or the heating mode, it is possible to selectively synthesize indole, indolone (1,5,6,7-tetrahydroindol-4-one), or cinnoline (5,6,7,8-tetrahydrocinnoline) derivatives in moderate to excellent yields.
Cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage
Zhang, Jianbo,Chang, Sukbok
supporting information, p. 12585 - 12590 (2020/08/21)
Described herein is the development of a borane-catalyzed cine-silylative ring-opening of α-methyl azacycles. This transformation involves four-step cascade processes: (i) exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of the resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of the terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal role in the β-amino elimination step.
Exploration and Development of a C-H-Activated Route to Access the [1,2]Dithiolo[4,3- b ]indole-3(4 H)-thione Core and Related Derivatives
Asquith, Christopher R. M.,Konstantinova, Lidia S.,Tizzard, Graham J.,Laitinen, Tuomo,Coles, Simon J.,Rakitin, Oleg A.,Hilton, Stephen T.
, p. 156 - 160 (2019/01/14)
A robust procedure for the production of [1,2]dithiolo[4,3- b ]indole-3(4 H)-thione analogues using a DABCO/S 2 Cl 2 complex as a sulfur source via a C-H activated approach.
Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage
Chen, Hongyi,Yang, Hongqin,Li, Nutao,Xue, Xinghua,He, Ze,Zeng, Qingle
, p. 1679 - 1685 (2019/08/20)
In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.
Pd-Catalyzed Dearomative Carboxylation of Indolylmethanol Derivatives
Mita, Tsuyoshi,Ishii, Sho,Higuchi, Yuki,Sato, Yoshihiro
supporting information, p. 7603 - 7606 (2018/12/11)
By using a new catalytic system (PdCl2[P(n-Bu)3]2 in combination with ZnEt2), various 3-indolylmethanol derivatives were successfully carboxylated with CO2 (1 atm) via dearomatization of the indole nucleus, affording 3-methyleneindoline-2-carboxylates. In contrast, carboxylation of 2-indolylmethanol derivatives afforded unexpected doubly carboxylated products, which are useful synthetic precursors for biologically active compounds.
Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates
Mandal, Tirtha,Chakraborti, Gargi,Karmakar, Shilpi,Dash, Jyotirmayee
, p. 4759 - 4763 (2018/08/24)
The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.
Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids
Das, Amrita,Watanabe, Kenji,Morimoto, Hiroyuki,Ohshima, Takashi
supporting information, p. 5794 - 5797 (2017/11/10)
Boronic acid was used to accelerate a three-component reaction of indoles, thiols, and glyoxylic acids for the synthesis of α-sulfanyl-substituted indole-3-acetic acids. Boronic acid catalysis to activate the α-hydroxy group in α-hydroxycarboxylic acid in
A facile and general acid-catalyzed deuteration at methyl groups of N-heteroarylmethanes
Liu, Min,Chen, Xue,Chen, Tieqiao,Yin, Shuang-Feng
supporting information, p. 2507 - 2511 (2017/04/03)
A facile and general Br?nsted acid-catalyzed deuteration at the methyl group of N-heteroarylmethanes was achieved through a dearomatic enamine intermediate under relatively mild reaction conditions. Both 2-methyl and 4-methyl groups in quinolines were deuterated with high deuterium incorporation. Pyridines, benzo[d]thiazoles, indoles and imines including these clinical drugs were also deuterated efficiently at the methyl groups. This reaction could be conducted on a large scale (500 mmol), showing its good potential for use in large-scale synthesis.
Electron-Transfer and Hydride-Transfer Pathways in the Stoltz–Grubbs Reducing System (KOtBu/Et3SiH)
Smith, Andrew J.,Young, Allan,Rohrbach, Simon,O'Connor, Erin F.,Allison, Mark,Wang, Hong-Shuang,Poole, Darren L.,Tuttle, Tell,Murphy, John A.
supporting information, p. 13747 - 13751 (2017/10/12)
Recent studies by Stoltz, Grubbs et al. have shown that triethylsilane and potassium tert-butoxide react to form a highly attractive and versatile system that shows (reversible) silylation of arenes and heteroarenes as well as reductive cleavage of C?O bonds in aryl ethers and C?S bonds in aryl thioethers. Their extensive mechanistic studies indicate a complex network of reactions with a number of possible intermediates and mechanisms, but their reactions likely feature silyl radicals undergoing addition reactions and SH2 reactions. This paper focuses on the same system, but through computational and experimental studies, reports complementary facets of its chemistry based on a) single-electron transfer (SET), and b) hydride delivery reactions to arenes.
