602-04-0Relevant academic research and scientific papers
Transformations of 6,7-difluoroquinoxaline with Indoles: Synthesis of Indole-Substituted 6,7-difluoroquinoxalines and Tris(indol-3-yl)methane Derivatives
Azev, Yu. A.,Ermakova,Ezhikova,Kodess,Berseneva,Kovalev
, (2017)
6,7-Difluoroquinoxaline (1) reacted with 1- and 2-methylindoles (2a and 2b) with heating in AcOH to give products from substitution of H in the heterocyclic fragment (3a and 3b) and tris(indol-3-yl)methane derivatives (4a and 4b).
An expeditious and efficient synthesis of symmetrical tris(indolyl)methanes under catalyst-free conditions in fluorinated alcohols
Khaksar, Samad,Vahdat, Seyed Mohammad,Gholizadeh, Mahnaz,Talesh, Saeed Mohammadzadeh
, p. 8 - 11 (2012)
Hexafluoro-2-propanol (HFIP) is explored as an effective medium for the synthesis of symmetrical tris(indolyl)methanes through the reaction of indole derivatives with orthoesters at room temperature. The solvent (HFIP) can be readily separated from reaction products and recovered in excellent purity for direct reuse.
Efficient and convenient method for the synthesis of symmetrical triindolylmethanes catalyzed by iodine
Zhang, Zhan-Hui,Lin, Jin
, p. 209 - 215 (2007)
Indoles reacted with triethyl orthoformate in the presence of a catalytic amount of iodine at room temperature to give the corresponding symmetrical triindolylmethanes (TIMs) in good to high yields. Copyright Taylor & Francis Group, LLC.
Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles
Noland, Wayland E.,Kumar, Honnaiah Vijay,Flick, Grant C.,Aspros, Cole L.,Yoon, Jong Hyeon,Wilt, Andre C.,Dehkordi, Nasim,Thao, Sheng,Schneerer, Andrew K.,Gao, Siming,Tritch, Kenneth J.
, p. 3913 - 3922 (2017/06/13)
Hydrated ferric sulfate [Fe2(SO4)3·xH2O] has been found to be an efficient catalyst for condensation of bisindoles or trisindoles with aliphatic or aryl aldehydes and ketones including methyl and ethyl-alkyl ketones, methyl aryl ketones, cyclic ketones, and 4-chromanones in 19–96% yields. Trisindoles and 2,2'-alkylidenebisindoles were obtained from indole-3-carbaldehydes or 3-methylindole in 72–84% yields. A total of 43 substrates was employed, giving 33 bisindoles, 3 trisindoles, and one 2:2 product; seventeen of these are new. The best results were obtained from heating ethanolic suspensions, with Fe2(SO4)3·xH2O loaded at 60 mg per mmol of electrophiles. The reaction times were typically 1–4 h, while hindered electrophiles required 8–24 h. These conditions were strong enough to promote 2:1 condensation of indole with substrates without forming higher-order byproducts, with few exceptions. This strategy features tolerance by the catalyst of a wide range of functional groups, readily available starting materials, simple operation, mild reaction conditions, and is environmentally friendly.
C-C bond cleavage: Metal-free-catalyzed reaction of Betti bases with various heterocycles under microwave irradiation
Deb, Mohit L.,Saikia, B.-Shriya,Borah, Kongkona,Baruah, Pranjal K.
supporting information, p. 1940 - 1946 (2016/11/25)
The reaction of Betti bases with various heterocycles in the presence of p-toluenesulphonic acid (PTSA) under microwave irradiation gives bis(heterocycle)methanes through benzyl transfer. The reaction proceeds via the cleavage of C-N bond followed by C-C
Synthesis of pharmacologically active bis(indolyl) and tris(indolyl) derivatives using chlorotrimethylsilane
Singh, Nongthombam G.,Kathing, Chingrishon,Rani, Jims W. S.,Nongkhlaw, Rishan L.
, p. 442 - 446 (2014/05/06)
Chlorotrimethylsilane is found to be a comparatively fast and efficient catalyst for carrying out electrophilic substitution reactions of indoles with various aldehydes/ketones/triethylorthoformate, yielding excellent amount of bis(indolyl)methanes/tris(indolyl)methanes. The merits of this protocol are avoidance of any external energy source, minimal reaction time, simple and easy procedure and high yield under solvent free room temperature condition. The versatility of this method has been tested with various aldehydes/ketones and received satisfactory results. A simple, fast, efficient, cheap and versatile method for the synthesis of bis(indolyl)methanes and tris(indolyl)methanes under solvent free room temperature condition using chlorotrimethylsilane as a catalyst has been developed. Thus, we have demonstrated the utility of TMSCl not only as a protecting group but also as catalyst in electrophilic substitution reactions. Copyright
Eco-friendly synthesis of condensed nitrogen heterocycles: A brief experience from our group
Chakrabarty, Manas,Mukherji, Ajanta
, p. 1681 - 1694 (2014/01/17)
In order to develop eco-friendly syntheses of condensed nitrogen heterocycles, solvent-free syntheses on solid acidic catalysts and aqueous reactions using a phase transfer catalyst (PTC) were successfully carried out. The catalysts used were (i) TLC-grade silica gel G (SiO2), (ii) SiO2 doped with 10 mol% phosphoric acid (H3PO 4-SiO2), (iii) Montmorillonite K10 clay (K10), (iv) acid-washed K10 clay (acid-clay), (v) K10 doped with one equivalent (with respect to substrate) of tosic acid (TsOH-K10) and (vi) cetylpyridinium bromide (CPB) (5 mol%) as the PTC. The reactions were carried out at room temperature (rt), at 60-70°C (oven) or under microwave irradiation (MWI).
A short, novel, and practical synthesis of 3-alkenylated indoles
Kargar, Mojgan,Hekmatshoar, Rahim,Mostashari, Abdol Jalil
, p. 1743 - 1749 (2013/05/21)
Direct metal-free alkenylation of 2-methylindole via acid-mediated Michael addition-elimination reaction with ethoxymethylenemalononitrile or ethyl ethoxymethylenecyanoacetate affords 3-indolyl-2-cyanoacrylonitrile and ethyl 3-indolyl-2-cyanoacrylate. Behavior of 1H-indole is predictably different. Copyright Taylor & Francis Group, LLC.
Synthesis of novel methylene bridge functionalized bis(indolyl)methanes thorough a double Michael addition
Kargar, Mojgan,Hekmatshoar, Rahim,Mostashari, Abdoljalil
, p. 2535 - 2546 (2012/01/13)
A simple synthesis of a series of novel diethyl bis(indol-3-yl)- methylmalonate is described. This involves domino Michael addition/elimination/ Michael addition of indoles to diethyl ethoxymethylenemalonate as double Michael acceptor.
Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles
Azev, Yuri A.,Shorshnev, Sergey V.,Golomolzin, Boris V.
body text, p. 2899 - 2903 (2009/09/08)
Reactions of quinazoline 1 with indole, pyrogallol and 1-phenyl-3-methylpyrazol-5-one in the presence of acid led to C-4 adducts 2, 3 and 5. Adduct 4 is formed by heating 1 with 1,3-dimethylbarbituric acid without acid catalysis. 1-Phenyl-3-methylpyrazol-
