883529-71-3Relevant academic research and scientific papers
A straightforward approach to tetrahydroindolo[3,2-b]carbazoles and 1-indolyltetrahydrocarbazoles through [3+3] cyclodimerization of indole-derived cyclopropanes
Ivanova, Olga A.,Budynina, Ekaterina M.,Khrustalev, Victor N.,Skvortsov, Dmitriy A.,Trushkov, Igor V.,Melnikov, Mikhail Ya.
, p. 1223 - 1227 (2016)
A rapid new approach to produce biologically relevant bisindoles, namely indolyltetrahydrocarbazoles and indolo[3,2-b]carbazoles, has been developed, based on the Ga(OTf)3-catalyzed [3+3] cyclodimerization of indole-derived donor-acceptor cyclopropanes. Chemoselectivity of the process depends on the location of the three-membered ring at the indole core. Gemination for creation: A new method for bisindole assembly was proposed through [3+3] cyclodimerization of indole-derived cyclopropanes. Variations in the cyclopropane position at the indole core fine-tune the process towards the selective formation of indolyltetrahydrocarbazoles or indolo[3,2-b]carbazoles.
Palladium-Catalyzed Benzannulations of 1-(Indol-2-yl)but-3-yn-1-ols: Easy Access to Functionalized Carbazoles
Pramanik, Subhendu,Chatterjee, Sarat,Banerjee, Rumjhum,Chowdhury, Chinmay
supporting information, p. 1895 - 1900 (2022/03/27)
An atom-economical direct synthesis of carbazoles having aryl and aryl ketone groups has been achieved through Pd(II)-catalyzed cascade reactions between 1-(indol-2-yl)but-3-yn-1-ols and aldehydes. The reaction proceeds through alkyne-carbonyl metathesis, an uncommon pathway using palladium catalysts, and constitutes a fast intermolecular assembly through four carbon-carbon bond formations in one pot. Absence of the aldehyde substrate resulted in the formation of C4-aryl-substituted carbazoles. The reaction is amenable to the synthesis of biscarbazole derivatives.
Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes
Faltracco, Matteo,Damian, Matteo,Ruijter, Eelco
supporting information, p. 7592 - 7596 (2021/10/12)
An alkylation/olefination cascade of indolecarboxaldehydes and phosphonate-functionalized donor-acceptor cyclopropanes affords functionalized dihydrocarbazoles and cyclohepta[cd]indoles in formal (3 + 3) and (4 + 3) cycloadditions. A minor modification to the reaction conditions also allows access to the fully aromatic heterocyclic scaffolds by thermal loss of an electron-rich aryl moiety.
Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics
Drew, Melanie A.,Arndt, Sebastian,Richardson, Christopher,Rudolph, Matthias,Hashmi, A. Stephen K.,Hyland, Christopher J. T.
, p. 13971 - 13974 (2019/11/25)
Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.
Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles
Wani, Imtiyaz Ahmad,Bhattacharyya, Aditya,Sayyad, Masthanvali,Ghorai, Manas K.
, p. 2910 - 2922 (2018/05/03)
Direct and expedient access to densely substituted tetrahydrocarbazoles and tetrahydrocycloheptadiindoles bearing multiple contiguous stereocentres has been achieved via a two-fold divergent diastereoselective (dr up to >99:1) transformation of 2-vinylindoles. The high-yielding conversions (yield up to 87%) that are amenable for a wide range of substituted 2-vinylindoles proceed through Lewis acid-catalyzed [4 + 2] and [4 + 3] cyclization-aromatization cascade reactions, respectively, involving a heretofore-unprecedented reversal of the polarity (umpolung) of 2-vinylindoles. The two synthetic routes are effortlessly transposable into each other by merely modulating the temperature to furnish the corresponding products in a selective and exclusive fashion. In addition, another novel synthetic route to tetrahydroindolocarbazoles has been developed that advances via a formal [4 + 2] cyclization of 4-vinylindoles involving sequential C3 Michael addition-dearomatization-aromatization cascade reactions.
Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones
Zhang, Kaifan,Xu, Xiaoying,Zheng, Jiuan,Yao, Hequan,Huang, Yue,Lin, Aijun
, p. 2596 - 2599 (2017/05/24)
A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca
Structure-activity relationship study of β-oxidation resistant indole-based 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) receptor antagonists
Ye, Qiuji,Chourey, Shishir,Wang, Rui,Chintam, Nagendra Reddy,Gravel, Sylvie,Powell, William S.,Rokach, Joshua
, p. 4770 - 4776 (2017/09/27)
5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is formed from 5S-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE) by the 5-lipoxygenase (5-LO) pathway under conditions associated with oxidative stress. 5-Oxo-ETE is an important pro-inflammatory mediator, which stimulates the migration of eosinophils via a selective G-protein coupled receptor, known as the OXE receptor (OXE-R). Previously, we designed and synthesized structural mimics of 5-oxo-ETE such as 1 using an indole scaffold. In the present work, we added various substituents at C-3 of this moiety to block potential β-oxidation of the 5-oxo-valerate side chain, and investigated the structure-activity relationships of the resulting novel β-oxidation-resistant antagonists. Cyclopropyl and cyclobutyl substituents were well tolerated in this position, but were less potent as the highly active 3S-methyl compound. It seems likely that 3-alkyl substituents can affect the conformation of the 5-oxovalerate side chain containing the critical keto and carboxyl groups, thereby affecting interaction with the OXE-receptor.
Pharmacokinetics and Metabolism of Selective Oxoeicosanoid (OXE) Receptor Antagonists and Their Effects on 5-Oxo-6,8,11,14-eicosatetraenoic Acid (5-Oxo-ETE)-Induced Granulocyte Activation in Monkeys
Cossette, Chantal,Chourey, Shishir,Ye, Qiuji,Nagendra Reddy, Chintam,Gore, Vivek,Gravel, Sylvie,Slobodchikova, Irina,Vuckovic, Dajana,Rokach, Joshua,Powell, William S.
, p. 10127 - 10146 (2016/12/07)
The potent eosinophil chemoattractant 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that acts via the selective OXE receptor, which is present in many species, but not rodents. We previously reported that the indole 230 is
Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines
Li, Long,Zhou, Bo,Wang, Yong-Heng,Shu, Chao,Pan, Yi-Fei,Lu, Xin,Ye, Long-Wu
, p. 8245 - 8249 (2015/07/07)
An efficient zinc(II)-catalyzed alkyne oxidation/C￡H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.
