80360-21-0Relevant articles and documents
Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon
Savvidou, Anatoli,IoannisTzaras, Dimitrios,Koutoulogenis, Giorgos S.,Theodorou, Alexis,Kokotos, Christoforos G.
supporting information, p. 3890 - 3897 (2019/06/27)
Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.
Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts
Jayaraman, Arumugam,Misal Castro, Luis C.,Fontaine, Frédéric-Georges
supporting information, p. 1489 - 1499 (2018/10/26)
A practical and scalable metal-free catalytic method for the borylation and borylative dearomatization of heteroarenes has been developed. This synthetic method uses inexpensive and conveniently synthesizable bench-stable precatalysts of the form 1-NHR2-2-BF3-C6H4, commercially and synthetically accessible heteroarenes as substrates, and pinacolborane as the borylation reagent. The preparation of several borylated heterocycles on 2 and 50 g scales was achieved under solvent-free conditions without the use of Schlenk techniques or a glovebox. A kilogram-scale borylation of one of the heteroarene substrates was also achieved using this cost-effective green methodology to exemplify the fact that our methodology can be conveniently implemented in fine chemical industries.
Total synthesis of calothrixin B and its analogs
Saravanan, Velu,Muthu Ramalingam, Bose,Mohanakrishnan, Arasambattu K.
, p. 1266 - 1279 (2014/03/21)
The total synthesis of calothrixin B and its analogs was achieved starting from 2-methylindole. The synthesis involved an electrocyclization of 2-nitroarylvinyl-3-phenylsulfonylvinylindoles as a key step to give 2-nitroaryl-4-methoxy-3-methylcarbazoles. Oxidation of these compounds followed by reductive cyclization led to N-phenylsulfonylquinocarbazoles. These quinocarbazoles underwent hydrolysis and aerial oxidation in one pot to give the target compounds. A linear synthesis of calothrixin B and its analogs has been established from commercially available 2-methylindole. The thermal electrocyclization of 2-nitroarylvinyl-3-phenylsulfonylindole was a key step in the synthesis. The synthesis of calothrixin B and its analogs was achieved in 12-22 % overall yield over twelve steps. Copyright
Total Synthesis of Calothrixin B and Its Analogs
Saravanan, Velu,Muthu Ramalingam, Bose,Mohanakrishnan, Arasambattu K.
, p. 1266 - 1279 (2015/10/05)
The total synthesis of calothrixin B and its analogs was achieved starting from 2-methylindole. The synthesis involved an electrocyclization of 2-nitroarylvinyl-3-phenylsulfonylvinylindoles as a key step to give 2-nitroaryl-4-methoxy-3-methylcarbazoles. Oxidation of these compounds followed by reductive cyclization led to N-phenylsulfonylquinocarbazoles. These quinocarbazoles underwent hydrolysis and aerial oxidation in one pot to give the target compounds.
Discovery of isoquinolinone indole acetic acids as antagonists of chemoattractant receptor homologous molecule expressed on TH2 cells (CRTH2) for the treatment of allergic inflammatory diseases
Kaila, Neelu,Follows, Bruce,Leung, Louis,Thomason, Jennifer,Huang, Adrian,Moretto, Alessandro,Janz, Kristin,Lowe, Michael,Mansour, Tarek S.,Hubeau, Cedric,Page, Karen,Morgan, Paul,Fish, Susan,Xu, Xin,Williams, Cara,Saiah, Eddine
, p. 1299 - 1322 (2014/03/21)
Previously we reported the discovery of CRA-898 (1), a diazine indole acetic acid containing CRTH2 antagonist. This compound had good in vitro and in vivo potency, low rates of metabolism, moderate permeability, and good oral bioavailability in rodents. H
N-ARYLSULFONYL-3-AMINOALKOXYINDOLES
-
Page 53-54, (2008/06/13)
The present invention describes substituted 3-Aminoalkoxyindoles, compounds of the general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bio-active metabolites and any suitable combination of the above. The invention also discloses the processes for preparing such compounds of the general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bio-active metabolites and also includes any suitable combination of the above. Further described are various methods of administering these compounds of general formula (I), i.e. pharmaceutically acceptable dosage forms, their composition and their use in either therapy or diagnosis.
Novel strategies for the solid phase synthesis of substituted indolines and indoles
Nicolaou,Roecker,Hughes, Robert,Van Summeren, Ruben,Pfefferkorn, Jeffrey A.,Winssinger, Nicolas
, p. 465 - 476 (2007/10/03)
Using a polymer-bound selenenyl bromide resin, o-allyl and o-prenyl anilines were cycloaded to afford a series of solid-supported indoline and indole scaffolds. These scaffolds were then functionalized and cleaved via four distinct methods, namely traceless reduction, radical cyclization, radical rearrangement, and oxidative elimination, to afford 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines, respectively. A number of small combinatorial libraries of compounds reminiscent of certain designed ligands of biological interest were constructed demonstrating the potential utility of the developed methodology to chemical biology studies and the drug discovery process.
Synthesis and cycloaddition of 2,4-dihydropyrroloindoles
Jeevanandam, Arumugasamy,Srinivasan, Panayencheri C.
, p. 2663 - 2666 (2007/10/02)
Friedel-Crafts acylation of 2-methyl-1-phenylsulfonylindole 6 gave the 3-acyl derivatives 7 which upon side chain bromination with N-bromosuccinimide (NBS) followed by treatment with primary amines afforded the title compounds 9.Diels-Alder reaction of 9 with dimethyl acetylenedicarboxylate (DMAD) gave the polysubstituted carbazoles 12.
Indole β-Nucleophilic Substitution. Part 7. β-Halogenation of Indoles. Attempted Intramolecular β-Nucleophilic Substitution of α-Arylindoles
Dalton, Lesley,Humphrey, Godfred L.,Cooper, Melanie M.,Joule, John A.
, p. 2417 - 2422 (2007/10/02)
Intramolecular β-nucleophilic substitution of 2-aryl-1-phenylsulphonylindoles could not be achieved.N-Arylsulphonylation of 2-arylindoles with arylsulphonyl halides using phase-transfer conditions is accompanied by 3-halogenation in some cases; the propor
