- An advantageous route to oxcarbazepine (Trileptal) based on palladium-catalyzed arylations free of transmetallating agents
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(Chemical Equation Presented) A new route to oxcarbazepine (Trileptal), the most widely prescribed antiepileptic drug, starting from commercially available 2′-aminoacetophenone and 1,2-dibromobenzene, is reported. The sequentially accomplished key steps are palladium-catalyzed intermolecular α-arylation of ketone enolates and intramolecular N-arylation reactions. After several experiments to establish the best conditions for both arylation processes, the target oxcarbazepine is obtained in a satisfactory overall yield, minimizing the number of steps and employing scalable catalytic procedures developed in partially aqueous media.
- Carril, Monica,SanMartin, Raul,Churruca, Fatima,Tellitu, Imanol,Dominguez, Esther
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Read Online
- One-pot synthesis of 2,3-disubstituted N-tosylindoles from o-acyl-N-tosylanilines
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The reaction of oacyl-N-tosylanilines with lithium trimethylsilyldiazomethane followed by treatment with t-BuLi and then electrophiles gave 2,3-disubstituted N-tosylindoles in a one-pot process. Georg Thieme Verlag Stuttgart.
- Hari, Yoshiyuki,Kanie, Tomoki,Miyagi, Takashi,Aoyama, Toyohiko
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Read Online
- Iron-Catalyzed Electrophilic Amination of Sodium Sulfinates with Anthranils
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A practical method for the synthesis of N-(2-carbonylaryl) benzenesulfonamides via an iron-catalyzed electrophilic amination of sodium sulfinates with anthranils is described. This redox-neutral transformation has high atom efficiency and is achieved under simple and mild reaction conditions. A wide range of anthranils and sodium sulfinates were compatible in this transformation. Moreover, the synthetic potential of this methodology was further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
- Liang, Baihui,Huang, Junjie,Zhu, Weidong,Li, Yawen,Jiang, Lanping,Gao, Yang,Xie, Feng,Li, Yibiao,Chen, Xiuwen,Zhu, Zhongzhi
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p. 1466 - 1473
(2021/02/09)
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- Synthesis method of o-acylaniline sulfonamide compound
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The invention discloses a synthesis method of a o-acylaniline sulfonamide compound. The preparation method is characterized by comprising the following steps: mixing a benzisoxazole compound as shownin a chemical formula I, a sodium sulfinate compound as shown in a chemical formula II, a metal catalyst and a solvent, and reacting to obtain the o-acylaniline sulfonamide compound as shown in a chemical formula III, in the formula, R1 is a monosubstituted or polysubstituted group on a benzene ring. The synthesis method can be used for efficiently synthesizing the o-acylaniline sulfonamide compound, has the advantages of simple synthesis steps, safety in operation, good compatibility of the synthesis method to functional groups and high atom economy, and is easy for industrial synthesis.
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Paragraph 0145-0151
(2020/10/30)
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- C-to N-Center Remote Heteroaryl Migration via Electrochemical Initiation of N Radical by Organic Catalyst
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Herein an exogenous oxidant- A nd metal-free electrochemical heteroaryl migration triggered by N radicals to construct new N-C bonds was developed. This methodology features a high atom economy and utilization rate of energy, and it is insensitive to water and air. Moreover, a user-friendly undivided cell was employed. The use of an organic catalyst makes it more efficient, green, and practical.
- Liu, Chengkou,Jiang, Qiang,Lin, Yang,Fang, Zheng,Guo, Kai
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supporting information
p. 795 - 799
(2020/02/04)
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- Visible-light-promoted N-centered radical generation for remote heteroaryl migration
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Herein, an efficient visible-light-mediated N-H heteroarylationviaremote heteroarylipso-migration has been accomplished. Moderate to good yields were obtained with good functional group tolerance. Moreover, a simple and readily available organic photoredox catalyst was employed, avoiding the use of complex and costly noble metal compounds.
- Cai, Chen,Fang, Zheng,Guo, Kai,Jiang, Qiang,Liu, Chengkou,Yuan, Chengcheng
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supporting information
p. 7663 - 7670
(2020/10/14)
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- Domino Aryne Annulation via a Nucleophilic-Ene Process
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1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.
- Xu, Hai,He, Jia,Shi, Jiarong,Tan, Liang,Qiu, Dachuan,Luo, Xiaohua,Li, Yang
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p. 3555 - 3559
(2018/03/21)
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- Manganese-Catalyzed ortho-C-H Amidation of Weakly Coordinating Aromatic Ketones
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An efficient manganese-catalyzed ortho-C-H amidation of weakly coordinating aromatic ketones using the readily available sulfonyl azide as the amination reagent is developed. The key step is the ketone directed aromatic metalation using the in situ generated reactive Mn intermediate, MnMe(CO)5. This method offers excellent chemical yields, high regioselectivities, and good functional group tolerance.
- Kong, Xianqiang,Xu, Bo
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supporting information
p. 4495 - 4498
(2018/08/07)
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- Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation
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In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).
- Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan
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supporting information
p. 4161 - 4167
(2018/09/21)
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- Nickel-Catalyzed Synthesis of Benzo[ b]naphtho[1,2- d]azepine via Intramolecular Radical Tandem Cyclization of Alkyl Bromide-Tethered Alkylidenecyclopropanes
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A Ni(II)-catalyzed tandem cyclopropane ring opening and radical alkylation of the aromatic ring using unactivated alkyl bromide-tethered alkylidenecyclopropanes (ACPs) have been described in this paper. This ring-forming process exhibits a broad substrate scope with a variety of primary alkyl bromides and aromatic rings, affording diversified benzo[b]naphtho[1,2-d]azepine derivatives in moderate-to-excellent yields under mild conditions. Plausible reaction mechanisms have been proposed on the basis of several control experiments, including the deuterium labeling examinations. Further derivatization of the obtained polycyclic product has also been performed.
- Jiang, Bo,Liu, Jia-Xin,Wei, Yin,Shi, Min
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supporting information
p. 6229 - 6233
(2018/10/05)
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- Diastereoselective synthesis of 2,4-substituted tetrahydroquinolines via hf(otf)4-catalyzed substitution/cyclization of 2-aminobenzyl alcohols with styrenes
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An efficient and convenient stereoselective synthetic approach to 2,4-substituted 1,2,3,4-tetrahydroquinoline has been developed. This catalytic procedure involves a sequential reaction of 2-aminobenzyl alcohol with styrenes in the presence of Hf(OTf)4 ca
- Noji, Masahiro,Kadowaki, Hiroto,Kubota, Yuuki,Yoshida, Tomomi,Saito, Noriko,Yamaguchi, Subaru,Ohata, Ren,Ishii, Keitaro,Takanami, Toshikatsu
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p. 1041 - 1073
(2017/07/27)
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- The Catalytic Mechanism of the Class C Radical S-Adenosylmethionine Methyltransferase NosN
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S-Adenosylmethionine (SAM) is one of the most common co-substrates in enzyme-catalyzed methylation reactions. Most SAM-dependent reactions proceed through an SN2 mechanism, whereas a subset of them involves radical intermediates for methylating non-nucleophilic substrates. Herein, we report the characterization and mechanistic investigation of NosN, a class C radical SAM methyltransferase involved in the biosynthesis of the thiopeptide antibiotic nosiheptide. We show that, in contrast to all known SAM-dependent methyltransferases, NosN does not produce S-adenosylhomocysteine (SAH) as a co-product. Instead, NosN converts SAM into 5′-methylthioadenosine as a direct methyl donor, employing a radical-based mechanism for methylation and releasing 5′-thioadenosine as a co-product. A series of biochemical and computational studies allowed us to propose a comprehensive mechanism for NosN catalysis, which represents a new paradigm for enzyme-catalyzed methylation reactions.
- Ding, Wei,Li, Yongzhen,Zhao, Junfeng,Ji, Xinjian,Mo, Tianlu,Qianzhu, Haocheng,Tu, Tao,Deng, Zixin,Yu, Yi,Chen, Fener,Zhang, Qi
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supporting information
p. 3857 - 3861
(2017/03/27)
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- Palladium nanoparticles as reusable catalyst for the synthesis of N-aryl sulfonamides under mild reaction conditions
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An efficient palladium nanoparticles-catalyzed N-arylation of sulfonamides and sulfonyl azides is described. This procedure serves as an active protocol for intermolecular C-N bond formation using Pd(OAc)2 in PEG-400 under air. Aryl bromides and triflates react at 35°C, while aryl chlorides require heating to 50°C and give the desired products only in low yields. This reaction proceeds smoothly in acceptable yields using low catalyst loading.
- Khalaj, Mehdi,Ghazanfarpour-Darjani, Majid,Talei Bavil Olyai, Mohamad Reza,Shamami, Sakineh Faraji
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p. 211 - 221
(2016/03/30)
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- Palladium-catalyzed N-arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes
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A palladium-catalyzed construction for N-arylsulfonamide from nitroarenes and arylsulfonyl hydrazides is developed. In this protocol, abundant and stable nitroarenes serve as the nitrogen sources by in situ reduction reaction of hydrogen released from arylsulfonyl hydrazides. No external oxidants or reductants are needed for this kind of transformation.
- Zhao, Feng,Li, Bin,Huang, Huawen,Deng, Guo-Jun
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p. 13010 - 13013
(2016/02/12)
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- A Palladium- and Copper-Catalyzed Synthesis of Dihydro[1,2-b]indenoindole-9-ol and Benzofuro[3,2-b]indolines: Metal-Controlled Intramolecular C-C and C-O Bond-Forming Reactions
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A palladium- and copper-catalyzed synthesis of dihydro[1,2-b]indenoindole-9-ol and benzofuro[3,2-b]indolines has been developed, whereby the same starting material is employed for the synthesis of both heterocyclic scaffolds and the selectivity of the pro
- Boominathan, Siva Senthil Kumar,Wang, Jeh-Jeng
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supporting information
p. 17044 - 17050
(2015/11/16)
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- Silver(I)-mediated C-H amination of 2-alkenylanilines: Unique solvent-dependent migratory aptitude
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A highly effective silver(I)-mediated C-H amination of 2-alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high-yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β-monosubstituted 2-alkenylanilines with solvent-dependence was demonstrated.
- Youn, So Won,Ko, Tae Yun,Jang, Min Jung,Jang, Su San
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supporting information
p. 227 - 234
(2015/01/30)
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- Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions
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An iridium-catalyzed direct C-H amidation of weakly coordinating substrates, in particular of those bearing ester and ketone groups, under very mild conditions has been developed. The observed high reaction efficiency was achieved by the combined use of acetic acid and lithium carbonate as additives. Copyright
- Kim, Jinwoo,Chang, Sukbok
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supporting information
p. 2203 - 2207
(2014/03/21)
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- Copper-catalyzed intramolecular oxidative C(sp3)-H amidation of 2-aminoacetophenones: Efficient synthesis of indoline-2,3-diones
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An efficient synthesis of diverse indoline-2,3-diones from 2-aminoacetophenones through copper-catalyzed intramolecular C(sp3)-H amidation is developed. The reaction proceeds in DMSO by using O2 as the sole oxidant to provide the desired products in moderate to good yields.
- Huang, Jinbo,Mao, Tingting,Zhu, Qiang
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supporting information
p. 2878 - 2882
(2014/05/20)
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- Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones
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C-H activation: The ruthenium-catalyzed direct sp2 C-H amidation of arenes by using sulfonyl azides as the amino source is presented (see scheme). A wide range of substrates were readily amidated including arenes bearing weakly coordinating groups. Synthetic utility of the thus obtained products was demonstrated in the preparation of biologically active heterocycles. Copyright
- Kim, Jiyu,Kim, Jinwoo,Chang, Sukbok
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supporting information
p. 7328 - 7333
(2013/06/27)
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- Ru(ii)-catalyzed intermolecular C-H amidation of weakly coordinating ketones
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An efficient Ru(ii)-catalyzed intermolecular amidation of weakly coordinating ketones with sulfonyl azides via C-H bond activation is described. The reaction proceeds with high functional group tolerance, providing a novel approach to practical ketone-directed intermolecular C-N bond formation in the absence of an additional oxidant.
- Zheng, Qing-Zhong,Liang, Yu-Feng,Qin, Chong,Jiao, Ning
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supporting information
p. 5654 - 5656
(2013/07/04)
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- Ru(ii)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
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Ru(ii)-catalyzed intermolecular ortho-C-H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C-N bond formation products in good yields.
- Bhanuchandra,Ramu Yadav,Rit, Raja K.,Rao Kuram, Malleswara,Sahoo, Akhila K.
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supporting information
p. 5225 - 5227
(2013/06/27)
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- 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
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A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Copyright
- Kothandaraman, Prasath,Koh, Bing Qin,Limpanuparb, Taweetham,Hirao, Hajime,Chan, Philip Wai Hong
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p. 1978 - 1985
(2013/03/14)
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- Metal-free synthesis of 1H-indole-2-carbaldehydes by N-iodosuccinimide- mediated cyclization of 1-(2′-anilinyl)prop-2-yn-1-ols in water. A formal synthesis of (R)-calindol
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A N-iodosuccinimide (NIS)-mediated method to prepare 1H-indole-2- carbaldehydes efficiently from cycloisomerization of 1-(2-aminophenyl)prop-2-yn- 1-ols is described. The reaction is operationally straightforward and accomplished in good to excellent yiel
- Kothandaraman, Prasath,Lauw, Sherman Jun Liang,Chan, Philip Wai Hong
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p. 7471 - 7480
(2013/08/23)
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- Hg(OTf)2-catalyzed vinylogous semi-pinacol rearrangement leading to 1,4-dihydroquinolines
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An efficient method for the construction of dihydroquinoline derivatives possessing a quaternary carbon center is developed by an application of Hg(OTf)2-catalyzed vinylogous semi-pinacol-type rearrangement. The reaction was found to be specifi
- Namba, Kosuke,Kanaki, Michika,Suto, Hiroki,Nishizawa, Mugio,Tanino, Keiji
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supporting information; experimental part
p. 1222 - 1225
(2012/05/20)
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- Silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop- 2-yn-1-ols to (Z)-2-methylene-1-sulfonylindolin-3-ols
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A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino) phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1- sulfonylindolin-3-ol to examples of other members of the indole family of compounds.
- Susanti, Dewi,Koh, Fujiet,Kusuma, Jeffrey Antonius,Kothandaraman, Prasath,Chan, Philip Wai Hong
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p. 7166 - 7175
(2012/10/29)
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- Electrophile-driven regioselective synthesis of functionalized quinolines
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Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties can be synthesized in moderate to excellent yields (up to 99%) by 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine (I2) under mil
- Ali, Shaukat,Zhu, Hai-Tao,Xia, Xiao-Feng,Ji, Ke-Gong,Yang, Yan-Fang,Song, Xian-Rong,Liang, Yong-Min
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supporting information; experimental part
p. 2598 - 2601
(2011/06/26)
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- Cyclopropyl carbinol rearrangement for benzo-fused nitrogen ring synthesis
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A synthetic method that relies on gold-catalysed cyclopropyl carbinol rearrangement of 2-tosylaminophenyl cyclopropylmethanols to prepare 2,3-dihydro-1H-benzo[b]azepines and 2-vinylindolines efficiently is reported. The reactions were shown to be chemoselective, with secondary and tertiary alcohol substrates exclusively providing benzo-fused five- and seven-membered ring products, respectively. The ring-forming process was also found to proceed in moderate to excellent yields under mild conditions only in the presence of the gold and silver catalyst combination. The mechanism is thought to involve activation of the alcohol by the (p-CF3C6H 4)3PAuCl/AgOTf (Tf=triflate) catalyst, resulting in ionization of the starting material. The tertiary carbocationic intermediate generated in situ in this manner then triggers ring-opening of the cyclopropane moiety and trapping by the tethered aniline group to give the 2,3-dihydro-1H-benzo[b]azepine. Cyclopropane ring fragmentation of the secondary carbocationic analogue, on the other hand, results in diene formation followed by subsequent intramolecular hydroamination to afford the 2-vinylindoline. Copyright
- Kothandaraman, Prasath,Huang, Chuhui,Susanti, Dewi,Rao, Weidong,Chan, Philip Wai Hong
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supporting information; experimental part
p. 10081 - 10088
(2011/10/09)
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- Gold-catalyzed cycloisomerizations of 1-(2-(Tosylamino)phenyl)prop-2-yn-1- ols to 1H-Indole-2-carbaldehydes and (E)-2-(Iodomethylene)Indolin-3-ols
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A method to prepare lH-indole-2-carbaldehydes and (E)-2-(iodomethylene) indolin-3-ols by gold(I)-catalyzed cycloisomerization of l-(2-(tosylamino) phenyl)prop-2-yn-1-ols with N-iodosuccinimide (NIS) is reported. The reactions were shown to be operationally simplistic and proceed efficiently for a wide variety of substrates, affording the corresponding products in good to excellent yields (70-99%). The mechanism is suggested to involve activation of the alkyne moiety of the substrate by the gold(I) catalyst. This triggers intramolecular addition of the tethered aniline moiety to give a vinyl gold intermediate, which undergoes iododeauration with NIS to give the (E)-2-(iodomethylene)indolin-3-ol adduct. Subsequent 1,3-allylic alcohol isomerization (1,3-AAI) followed by formylation of this vinyl iodide intermediate then gives the 1H-indole-2-carbaldehyde.
- Kothandaraman, Prasath,Mothe, Srinivasa Reddy,Toh, Sharon Si Min,Chan, Philip Wai Hong
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experimental part
p. 7633 - 7640
(2011/11/12)
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- Copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols as an expedient route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines
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A new efficient synthetic route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines that relies on copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols under mild and operationally straightforward conditions is
- Rao, Weidong,Kothandaraman, Prasath,Koh, Chii Boon,Chan, Philip Wai Hong
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supporting information; experimental part
p. 2521 - 2530
(2011/02/21)
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- Synthesis of benzazepines by gold-catalysed reactions of N-allenylamides
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The gold-catalysed reactions of alleneamides give different products depending on the substrate and the reaction conditions. In particular, N-(2-alkynylphenyl)-N-allenyltosylamides give benzazepines when using gold(III) catalysts in the presence of nucleophiles. This sequential process may follow two different reaction pathways, and these are discussed. Metal coordination to the alkyne followed by nucleophilic attack of the aliene and trapping of the intermediate with NuH accounts for the formation of 4, but coordination to the aliene and addition of NuH to give 3, which can decompose into other products and also form 4, is postulated as a better explanation for these results.
- Gonzalez-Gomez, Alvaro,Dominguez, Gema,Perez-Castells, Javier
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scheme or table
p. 5057 - 5062
(2010/02/28)
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- Copper-catalyzed N-Allenylation of allylic sulfonamides
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Figur Presented Allylic allenic amides have been synthesized via a copper-catalyzed cross-coupling between allylic sulfonamides and bromoallenes in moderate to good yields. Copper(I) thiophene-2-carboxylate (CuTC) was used a source of copper with DMEDA as the ligand. The allenylated products obtained are potential substrates for palladium-catalyzed carbocyclizations.
- Persson, Andreas K. A.,Johnston, Eric V.,Baeckvall, Jan-E.
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supporting information; experimental part
p. 3814 - 3817
(2009/12/06)
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- Sequential palladium-catalysed C- and N-arylation reactions as a practical and general protocol for the synthesis of the first series of oxcarbazepine analogues
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The first series of oxcarbazepine analogues, starting from readily-available materials and through a high-yielding five-step sequence based on palladium catalysis, is reported. The so-obtained compounds incorporate not only a variety of substituents in both of?the aryl rings comprising the framework of an oxcarbazepine, but also involve the more challenging palladium-catalysed coupling of a number of heteroaromatic substrates. The addition of small amounts of water in some of the metal-catalysed processes showed a beneficial effect, highly increasing the selectivity of such reactions.
- Carril, Mónica,SanMartin, Raul,Domínguez, Esther,Tellitu, Imanol
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p. 690 - 702
(2007/10/03)
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- β-cyclodextrin-catalyzed monosulfonylation of amines and amino acids in water
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A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.
- Sridhar,Srinivas,Kumar, V. Pavan,Narender,Rao, K. Rama
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p. 1873 - 1876
(2008/09/16)
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- Development of radical addition-cyclization-elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline
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Radical addition-cyclization-elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying unsaturated ester proceeded stereoselectively to give cis-furoquinolines and cis-hydroxyesters. The RACE reactions by using each of Bu3SnNMe2, Bu3SnD, and/or D2O were also examined in order to propose a reaction pathway to N-norpyrroloquinoline. Furthermore, the synthetic utility of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of (±)-martinelline.
- Miyata, Okiko,Shirai, Atsushi,Yoshino, Shintaro,Nakabayashi, Toshiki,Takeda, Yoshifumi,Kiguchi, Toshiko,Fukumoto, Daisuke,Ueda, Masafumi,Naito, Takeaki
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p. 10092 - 10117
(2008/02/13)
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- A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): Its application to the synthesis of key intermediates for anti-malarial agents
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A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2- dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology.
- Theeraladanon, Chumpol,Arisawa, Mitsuhiro,Nishida, Atsushi,Nakagawa, Masako
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p. 3017 - 3035
(2007/10/03)
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- Direct conversion of azides to carbamates and sulfonamides using Fe/NH4Cl: Effect of sonication
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A simple, direct and effective conversion of azides to carbamates and sulfonamides is achieved using Fe/NH4Cl in methanol. The influence of sonication and direct application in solution phase combinatorial chemistry are also studied by developing a 6x4 matrix library. (C) 2000 Elsevier Science Ltd.
- Chandrasekhar,Narsihmulu
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p. 7969 - 7972
(2007/10/03)
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- The Intramolecular Nitrile Oxide Cycloaddition Approach to the Mitomycins
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The construction of a benzazocine intermediate by the intramolecular nitrile oxide cycloaddition process has been examined as a possible approach to the mitomycins.
- Kozikowski, Alan P.,Mugrage, Benjamin B.
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p. 198 - 200
(2007/10/02)
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