- Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors
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Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.
- Prusty, Namrata,Kinthada, Lakshmana K.,Meena, Rohit,Chebolu, Rajesh,Ravikumar, Ponneri Chandrababu
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p. 891 - 905
(2021/02/09)
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- Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?
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Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.
- Chen, Xiao-Yue,Huang, Yu-Hao,Zhou, Jian,Wang, Peng
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supporting information
p. 1269 - 1272
(2020/08/13)
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- Seven-membered rings through metal-free rearrangement mediated by hypervalent iodine
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A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) med
- Silva, Siguara Bastos Lemos,Torre, Adriana Della,De Carvalho, Joo Ernesto,Ruiz, Ana Lcia Tasca Gois,Silva, Luiz F.
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p. 1475 - 1494
(2015/01/30)
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- Building a sulfonamide library by eco-friendly flow synthesis
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A rapid and eco-friendly synthesis of a sulfonamide library under flow conditions is described. The study illustrates an efficient, safe, and easily scalable preparation of sulfonamides by use of a meso-reactor apparatus, thus demonstrating the impact of flow technologies within drug discovery. Waste minimization, employment of green media, and nontoxic reactants are achieved by the optimization of the flow setup and experimental protocol designed to sequentially synthesize primary, secondary, and tertiary sulfonamides. Isolation of the products involves only extraction and precipitation affording pure compounds in good to high yields without further purification for biological evaluation.
- Gioiello, Antimo,Rosatelli, Emiliano,Teofrasti, Michela,Filipponi, Paolo,Pellicciari, Roberto
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supporting information
p. 235 - 239
(2013/06/27)
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- Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature
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A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given. Copyright
- Yan, Chang-Song,Peng, Yu,Xu, Xiao-Bo,Wang, Ya-Wen
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p. 6039 - 6048
(2012/06/18)
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- CsF-Celite as an efficient heterogeneous catalyst for sulfonylation and desulfonylation of heteroatoms
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CsF-Celite is found to be as an efficient reusable catalyst for sulfonylation and desulfonylation of heteroatoms. Sulfonamides and N-acylsulfonamides deprotect efficiently in the presence of CsF-Celite under solvent free conditions to give the free amines or amides in good to excellent yields.
- Tamaddon, Fatemeh,Nasiri, Alireza,Farokhi, Somayeh
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experimental part
p. 1477 - 1482
(2012/06/18)
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- Design, synthesis and 3-d characterization of 1-benzenesulfonyl-1,2,3,4-tetrahydroquinolines as lead scaffold for antiparasitic drug
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Ten 1-benzenesulfonyl-1,2,3,4-tetrahydroquinoline (BSTHQ) were synthesized and characterized and their antiprotozoal activities were investigated. This small library was designed by combining two chemical moieties that are known to be biologically active
- Pagliero,Pierini,Brun,Mazzieri
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experimental part
p. 461 - 470
(2011/10/18)
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- Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group
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Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides was successfully carried out by a constant current electrolysis using an undivided cell equipped with a platinum cathode and a magnesium anode in the presence of an arene mediator. The deprotection proceeded efficiently and selectively under neutral and mild conditions with a stoichiometric amount of electricity without the use of an Hg cathode to obtain the corresponding secondary amines in good to excellent yields.
- Senboku, Hisanori,Nakahara, Kazuo,Fukuhara, Tsuyoshi,Hara, Shoji
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supporting information; experimental part
p. 435 - 438
(2010/03/04)
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- Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent
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ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides.
- Aikawa, Haruo,Tago, Sakie,Umetsu, Kazuteru,Haginiwa, Naomichi,Asao, Naoki
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experimental part
p. 1774 - 1784
(2009/06/20)
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- Facile preparation of 3,4-dihydro-2,1-benzothiazine 2,2-dioxides and related reaction with 1,3-diiodo-5,5-dimethylhydantoin under photochemical conditions
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3,4-Dihydro-2,1-benzothiazine 2,2-dioxides were easily obtained in good yields by the reaction of N-methyl 2-arylethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation with a tungsten lamp. When N-benzyl 2-phenylethanesulfonamide
- Moroda, Atsushi,Furuyama, Shusuke,Togo, Hideo
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experimental part
p. 1336 - 1340
(2009/11/30)
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- Catalytic activation of the leaving group in the SN2 reaction
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A novel catalytic activation of the leaving group in the SN2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)2 to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives resulted in inversion of stereochemistry, which is a definitive feature of the S N2 reaction. The procedure is applicable for benzoazepine synthesis.
- Yamamoto, Hirofumi,Pandey, Ghanshyam,Asai, Yumiko,Nakano, Mayo,Kinoshita, Atsushi,Namba, Kosuke,Imagawa, Hiroshi,Nishizawa, Mugio
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p. 4029 - 4032
(2008/02/10)
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- Palladium catalysed aryl amination reactions in supercritical carbon dioxide
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Palladium catalysed C-N bond formation in supercritical carbon dioxide has been accomplished. Carbamic acid formation is avoided in part through the use of an N-silylamine as the coupling partner. Employing a catalyst system of Pd 2dba3 (1 mol%) and 2-dicyclohexylphosphino-2′, 4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (2 mol%) enabled the catalytic amination of aryl bromides and chlorides with N-silylanilines to be realised in excellent yield. Extension of the methodology to the N-arylation of N-silyldiarylamines, N-silylazoles and N-silylsulfonamides is reported. The Royal Society of Chemistry 2005.
- Smith, Catherine J.,Tsang, Melanie W.S.,Holmes, Andrew B.,Danheiser, Rick L.,Tester, Jefferson W.
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p. 3767 - 3781
(2007/10/03)
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- METHODS OF AMINATION
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A method of synthesising a compound of formula I: comprising the step of reacting a moiety of formula II: with a moiety of formula III: in compressed carbon dioxide in the presence of a transition metal catalyst and a base, wherein L is a labile leaving group; RN1 is optionally substituted C5-20 aryl; RN2is selected from optionally substituted C5-20aryl, optionally substituted C3-20 heterocyclyl, optionally substituted C3-7 alkyl, and optionally substituted sulfonyl; RN3 is selected from H and optionally substituted C1-7 alkyl, C3-20 heterocyclyl and C5-20aryl; or RN2 and RN3 together with the nitrogen atom to which they are attached form optionally substituted nitrogen-containing C3-20heterocylyl or C5-20 heteroaryl; and R1 R2 and R3 are independently selected from optionally substituted C1-7alkyl, C5-20 aryl, C3-20 heterocyclyl, hydroxy, halo, amino and C1-7 alkoxy, or two of R1, R2 and R3, together with the silicon atom to which they are attached, may form a silicon containing C5-7 heterocyclyl group.
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Page/Page column 30
(2010/02/14)
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- Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes
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Sulfonamides of primary amines bearing an aromatic ring at the γ-position were treated with (diacyloxyiodo)arenes and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. Here, the reactivity depends on the Z-group (protecting group) of the starting amides. Under the same reaction conditions, some sulfonamides were treated with (diacetoxyiodo)benzene and iodine in the presence of aromatics to give the corresponding N-arylated amides. These reactions proceed through the intramolecular and intermolecular amidations onto aromatic rings via the sulfonamidyl radicals formed.
- Togo, Hideo,Hoshina, Yoichiro,Muraki, Takahito,Nakayama, Hiromasa,Yokoyama, Masataka
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p. 5193 - 5200
(2007/10/03)
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- Intramolecular palladium-catalyzed aryl amination and aryl amidation
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Upon treatment with a palladium catalyst and a suitable base, aromatic halides undergo intramolecular substitution to form five, six, and seven-membered rings. In a similar fashion aryl halides with pendant amides or sulfonamides are cyclized to form five and six-membered rings.
- Wolfe, John P.,Rennels, Roger A.,Buchwald, Stephen L.
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p. 7525 - 7546
(2007/10/03)
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- Cyclic amination onto aromatic ring of sulfonamides with (diacetoxyiodo)arenes: Effect of sulfonyl group
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Sulfonamides of primary amine bearing an aromatic ring at γ-position were treated with (diacetoxyiodo)arene and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good
- Togo, Hideo,Hoshina, Yoichiro,Yokoyama, Masataka
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p. 6129 - 6132
(2007/10/03)
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