- Synthesis of benzannelated sultams by intramolecular Pd-catalyzed arylation of tertiary sulfonamides
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A new and efficient approach to five- and six-membered benzannelated sultams by intramolecular C-arylation of tertiary 1-(methoxycarbonyl)methanesulfonamides under palladium catalysis is described. In case of the α-toluenesulfonamide derivative, an unexpected formation of a 2,3-diarylindole was observed under the same conditions.
- Rassadin, Valentin A.,Scholz, Mirko,Klochkova, Anastasiia A.,De Meijere, Armin,Sokolov, Victor V.
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- Dual Photoredox/Cobaloxime Catalysis for Cross-Dehydrogenative α-Heteroarylation of Amines
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We report a dual-catalytic platform for the cross-dehydrogenative-coupling between (benzo-)thiazoles and amines which combines low loadings of an iridium photoredox catalyst and a cobaloxime catalyst under blue light irradiation. This transformation occurs without stoichiometric oxidants, giving products in moderate to excellent yields. DFT calculations support the key role of Co(II) for rearomatization of the radical-addition intermediate to generate the product.
- Bergamaschi, Enrico,Weike, Christopher,Mayerhofer, Victor J.,Funes-Ardoiz, Ignacio,Teskey, Christopher J.
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- IRAK DEGRADERS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00803; 0083-0085
(2021/06/26)
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- IRAK DEGRADERS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00512; 00704-00706
(2021/06/26)
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- Oxidative Pictet-Spengler cyclisations through acceptorless iridium-catalysed dehydrogenation of tertiary amines
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The valuable tetrahydro-β- and γ-carboline skeleta can be accessed through Pictet-Spengler cyclisation initiated by acceptorless dehydrogenation of saturated cyclic amines. The substrate scope for the β-isomers is found to be somewhat limited, but access
- Cooksey, John P.,Saidi, Ourida,Williams, Jonathan M.J.,Blacker, A. John,Marsden, Stephen P.
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supporting information
(2020/12/14)
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- A Diastereoselective Route to Benzoannelated Bridged Sultams
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A practical diastereoselective method for the synthesis of benzoannelated tri- and tetracyclic bridged sultams has been developed. The synthetic route employs widely available, substituted -iodoanilines and is based on intramolecular Michael addition followed by cycloalkylation with dihaloalkanes, or vice versa. The target compounds were isolated in good yields and the diastereoselectivity of the reaction could be easily controlled by the order of Michael addition and cycloalkylation steps.
- Klochkova, Anastasiia A.,Rassadin, Valentin A.,Sokolov, Victor V.
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supporting information
p. 4484 - 4494
(2021/08/13)
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- Modular counter-Fischer?indole synthesis through radical-enolate coupling
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A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
- Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
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supporting information
p. 1096 - 1102
(2021/01/26)
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- Antituberculosis Activity of the Antimalaria Cytochrome bcc Oxidase Inhibitor SCR0911
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The ability to respire and generate adenosine triphosphate (ATP) is essential for the physiology, persistence, and pathogenicity of Mycobacterium tuberculosis, which causes tuberculosis. By employing a lead repurposing strategy, the malarial cytochrome bc
- Bates, Roderick W.,Chong, Shi Min Sherilyn,Cook, Gregory M.,Dick, Thomas,Grüber, Gerhard,Harold, Liam K.,Manimekalai, Malathy Sony Subramanian,Pethe, Kevin,Sarathy, Jickky Palmae,Williams, Zoe C.
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p. 725 - 737
(2020/04/30)
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- Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
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The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
- Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
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supporting information
p. 4941 - 4948
(2019/11/03)
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- A General Copper Catalyst for Photoredox Transformations of Organic Halides
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A broadly applicable copper catalyst for photoredox transformations of organic halides is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl halides were shown to be smoothly activated through a rare Cu(I)/Cu(I)?/Cu(0) catalytic cycle. This complex efficiently catalyzes a series of radical processes, including reductions, cyclizations, and direct arylation of arenes.
- Michelet, Bastien,Deldaele, Christopher,Kajouj, Sofia,Moucheron, Cécile,Evano, Gwilherm
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supporting information
p. 3576 - 3579
(2017/07/17)
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- Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
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A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
- Praveen, Chandrasekar,Perumal
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p. 855 - 864
(2016/03/15)
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- Highly regioselective indoline synthesis under nickel/photoredox dual catalysis
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Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indic
- Tasker, Sarah Z.,Jamison, Timothy F.
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supporting information
p. 9531 - 9534
(2015/08/18)
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- Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives
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A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.
- Gronnier, Colombe,Boissonnat, Guillaume,Gagosz, Fabien
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supporting information
p. 4234 - 4237
(2013/09/12)
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- Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene
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Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.
- Shen, Hao,Vollhardt, K. Peter C.
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supporting information; experimental part
p. 208 - 214
(2012/03/11)
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- Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks
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An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate α-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products. Copyright
- Wetzel, Alexander,Gagosz, Fabien
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supporting information; experimental part
p. 7354 - 7358
(2011/09/16)
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- Total synthesis of tryprostatins A and B
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Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fuerstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.
- Yamakawa, Takayuki,Ideue, Eiji,Iwaki, Yuzo,Sato, Ayumu,Tokuyama, Hidetoshi,Shimokawa, Jun,Fukuyama, Tohru
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experimental part
p. 6547 - 6560
(2011/09/20)
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- Total synthesis of tryprostatins a and b
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A reasonable approach to the radical: The establishment of reliable conditions for the radical-mediated construction of indoles enabled the highly efficient synthesis of tryprostatins A and B. Use of the radical initiator 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) has allowed to carry out the radical cyclization at just 30°C, thereby suppressing the formation of by-products. Copyright
- Yamakawa, Takayuki,Ideue, Eiji,Shimokawa, Jun,Fukuyama, Tohru
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supporting information; experimental part
p. 9262 - 9265
(2011/02/25)
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- Richter cyclization and co-cyclization reactions of triazene-masked diazonium ions
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The conventional Richter cyclization involves diazotization of 2-alkynylanilines with HX (aq) (X = Br or Cl) and NaNO2, followed by spontaneous ring closure to give a mixture of 4-halocinnoline and 4-cinnolinone products. The different products
- Goeminne, Annelies,Scammells, Peter J.,Devine, Shane M.,Flynn, Bernard L.
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supporting information; experimental part
p. 6882 - 6885
(2011/03/18)
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- Preparation of 3-substituted-2-pyridin-2-ylindoles: regioselectivity of Larock's indole annulation with 2-alkynylpyridines
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A regioselective Larock approach to 3-substituted-2-pyridin-2-ylindoles from 2-alkynylpyridines and 2-iodoanilines is described herein. The unexpectedly high regioselectivity can be rationalized by a combination of steric, coordinative and electronic effects.
- Roschangar, Frank,Liu, Jianxiu,Estanove, Emilie,Dufour, Marine,Rodríguez, Sonia,Farina, Vittorio,Hickey, Eugene,Hossain, Azad,Jones, Paul-James,Lee, Heewon,Lu, Bruce Z.,Varsolona, Richard,Schr?der, Jürgen,Beaulieu, Pierre,Gillard, James,Senanayake, Chris H.
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p. 363 - 366
(2008/09/17)
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- Convergent synthesis of the quinolone substructure of BILN 2061 via carbonylative sonogashira coupling/cyclization
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A convergent synthesis of quinolone 2 (key substructure of the protease inhibitor BILN 2061) was developed via palladium-catalyzed carbonylation of 2-iodo-5-methoxy-aniline (4) with thiazolylacetylene 5.
- Haddad, Nizar,Tan, Jonathan,Farina, Vittorio
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p. 5031 - 5034
(2007/10/03)
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- Synthesis of ring-A-substituted tryptophan by a palladium-catalyzed heteroannulation reaction
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Coupling of substituted o-iodoanilines with methyl (S)-2-N,N-di-tert- butoxycarbonyl-5-oxo-pentanoate, derived from glutamic acid, in DMF in the presence of palladium acetate and DABCO provides substituted tryptophans in good to excellent yields. Georg Thieme Verlag Stuttgart.
- Jia, Yanxing,Zhu, Jieping
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p. 2469 - 2472
(2007/10/03)
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- Novel indole-based peroxisome proliferator-activated receptor agonists: Design, SAR, structural biology, and biological activities
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The synthesis and structure-activity relationship studies of novel indole derivatives as peroxisome proliferator-activated receptor (PPAR) agonists are reported. Indole, a druglike scaffold, was studied as a core skeleton for the acidic head part of PPAR
- Mahindroo, Neeraj,Huang, Chien-Fu,Peng, Yi-Huei,Wang, Chiung-Chiu,Liao, Chun-Chen,Lien, Tzu-Wen,Chittimalla, Santhosh Kumar,Huang, Wei-Jan,Chai, Chia-Hua,Prakash, Ekambaranellore,Chen, Ching-Ping,Hsu, Tsu-An,Peng, Cheng-Hung,Lu, I-Lin,Lee, Ling-Hui,Chang, Yi-Wei,Chen, Wei-Cheng,Chou, Yu-Chen,Chen, Chiung-Tong,Goparaju, Chandra M. V.,Chen, Yuan-Shou,Lan, Shih-Jung,Yu, Ming-Chen,Chen, Xin,Chao, Yu-Sheng,Wu, Su-Ying,Hsieh, Hsing-Pang
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p. 8194 - 8208
(2007/10/03)
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- BENZOFUSED HETEROARYL AMIDE DERIVATIVES OF THIENOPYRIDINES USEFUL AS THERAPEUTIC AGENTS, PHARMACEUTICAL COMPOSITIONS INCLUDING THE SAME, AND METHODS FOR THEIR USE
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The invention relates to compounds represented by the formula I and to prodrugs or metabolites thereof, or pharmaceutically acceptable salts or solvates of said compounds, said prodrugs, and said metabolites, wherein Z, Y, R11 and R14, R15, R16, and R17 are as defined herein. The invention also relates to pharmaceutical compositions containing the compounds of formula I and to methods of treating hyperproliferative disorders in a mammal by administering the compounds of formula I.
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- Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction
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A novel and concise synthesis of optically active tryptophan derivatives was developed via a palladium-catalyzed heteroannulation reaction of substituted o-iodoanilines with an internal alkyne. The required internal alkyne 14a or 25 was prepared in greater than 96% de via alkylation of the Schoellkopf chiral auxiliary 19 employing diphenyl phosphate as the leaving group. The Schoellkopf chiral auxiliary was chosen here for the preparation of L-tryptophans would be available from D-valine while the D-isomers required for natural product total synthesis would originate from the inexpensive L-valine (300-g scale). Applications of the palladium-catalyzed heteroannulation reaction were extended to the first asymmetric synthesis of L-isotryptophan 38 and L-benz[f]tryptophan 39. More importantly, the optically pure 6-methoxy-D-tryptophan 62 was prepared by this protocol on a large scale (>300 g). This should permit entry into many ring-A oxygenated indole alkaloids when coupled with the asymmetric Pictet-Spengler reaction. In addition, an improved total synthesis of tryprostatin A (9a) was accomplished in 43% overall yield employing this palladium-mediated process.
- Ma,Liu,Li,Flippen-Anderson,Yu,Cook
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p. 4525 - 4542
(2007/10/03)
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- Iodination with Potassium Permanganate/Hydroiodic Acid/Acetonitrile Reagent
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Iodination of various aromatic amines proceeds smoothly with a preformed homogeneous mixture of hydroiodic acid potassium permanganate in acetonitrile. para-Substituted products were obtained in high yields (71-78%) within twelve hours at room temperature. With a slight modification of the permanganate, hydroiodic acid and substrate ratio, iodination of alkynes to vic-diiodoalkenes can be carried out at 60 °C in 65-87% yield.
- Chen, Jyh-An,Lin, Ching-Shan,Liu, Lilian Kao
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- Consice Synthesis of CC-1065/Duocarmycin Pharmacophore Using the Intramolecular Heck Reaction
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3-Methyleneindoline derivatives were synthesized by intramolecular Heck reaction of N-allyl-2-iodoaniline derivatives in the presence of Ag2CO3.This method was successfully applied to the synthesis of the CC-1065/duocarmycin pharmacophore.
- Sakamoto, Takao,Kondo, Yoshinori,Uchiyama, Masanobu,Yamanaka, Hiroshi
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p. 1941 - 1942
(2007/10/02)
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