- Haloamines as Bifunctional Reagents for Oxidative Aminohalogenation of Maleimides
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An unprecedented copper-catalyzed oxidative aminohalogenation of electron-deficient maleimides with secondary amines and NXS (X = Cl, Br, I) was developed, in which the N-X bonds generated in situ were used as difunctionalized reagents. The distinctive features of this multicomponent reaction include a simple green catalytic system, a spectral substrate range, and the late-stage modification of drug molecules. Most importantly, this umpolung radical cascade strategy exploits the in situ formation of N-iodoamines that enable efficient alkene aminoiodination.
- Zhou, Xueying,Yao, Yujing,Wang, Caihong,Xu, Yaling,Zhang, Wenliang,Ma, Yunfei,Wu, Ge
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supporting information
p. 3669 - 3673
(2021/05/10)
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- Two-step continuous flow synthesis of amide via oxidative amidation of methylarene
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A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.
- Fang, Zheng,Guo, Kai,He, Wei,Liu, Chengkou,Shi, Tingting,Yang, Yuhang,Yang, Zhao,Zhang, Zhimin
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supporting information
(2020/02/28)
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- Synthesis of aromatic sulfonamides through a copper-catalyzed coupling of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-Chloroamines
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A copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-chloroamines is described. This coupling reaction provides an efficient and simple approach to a wide range of sulfonamides in moderate to good yields under mild conditions. Mechanistic investigation suggests that a radical process and transition-metal catalysis are merged in this tandem reaction.
- Zhang, Feng,Zheng, Danqing,Lai, Lifang,Cheng, Jiang,Sun, Jiangtao,Wu, Jie
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supporting information
p. 1167 - 1170
(2018/02/23)
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- A green, isocyanide-based three-component reaction approach for the synthesis of multisubstituted ureas and thioureas
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A one-pot, isocyanide based multicomponent protocol was presented starting from secondary amines towards (thio)urea derivatives and utilized for the construction of a diverse 27-membered chemical library. Following a green compatible microwave assisted condition, the formed N,N′-multisubstituted (thio)ureas were obtained in up to 85% yield.
- Angyal, Anikó,Demjén, András,W?lfling, János,Puskás, László G.,Kanizsai, Iván
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supporting information
p. 54 - 57
(2017/12/28)
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- Aryne Trifunctionalization Enabled by 3-Silylaryne as a 1,2-Benzdiyne Equivalent
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An unprecedented aryne 1,2,3-trifunctionalization protocol from 2,6-bis(silyl)aryl triflates was developed under transition-metal-free conditions. The reaction of generated 3-silylaryne with both pyridine N-oxide and N-hydroxylamide afforded o-silyl triflate/tosylate in a one-pot transformation, allowing the formation of 2,3-aryne precursors with various vicinal pyridinyl/amido substituents. These pyridinyl-substituted 2,3-aryne intermediates exhibit a broad scope of reactivity with diverse arynophiles in good yields and high selectivity.
- Lv, Chunjie,Wan, Caiwen,Liu, Song,Lan, Yu,Li, Yang
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supporting information
p. 1919 - 1923
(2018/04/16)
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- Copper-catalyzed one-pot oxidative amidation between methylarenes and amines
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A new method for the direct one-pot oxidative amidation between methylarenes and amines catalyzed by copper has been developed. This method integrates methylarene oxidation and amide bond formation, which are usually accomplished separately, into a single operation. In addition, the reaction provides a relatively high yield and has a wide substrate scope. Moreover, the starting reagents are abundant and available in a convenient way at a cheaper price.
- Yang, Yuhang,Gu, Jiajia,Fang, Zheng,Yang, Zhao,Wei, Ping,Guo, Kai
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p. 22797 - 22801
(2017/07/10)
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- Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C-H activation
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A one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, was developed. This cross-coupling reaction integrates alcohol oxidation and amide bond formation, which are usually accomplished separately, into a single operation. And it was green, simple and convenient, which has a wide substrate scope and makes use of cheap, abundant, and easily available reagents. The practical value of this method is highlighted through the synthesis of a high-profile pharmaceutical agent, acetylprocainamide.
- Gu, Jiajia,Fang, Zheng,Yang, Yuhang,Yang, Zhao,Wan, Li,Li, Xin,Wei, Ping,Guo, Kai
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p. 89413 - 89416
(2016/10/03)
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- Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors
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The continuous flow synthesis of a range of organic solutions of N,N-dialkyl-N-chloramines is described using either a bespoke meso-scale tubular reactor with static mixers or a continuous stirred tank reactor. Both reactors promote the efficient mixing of a biphasic solution of N,N-dialkylamine in organic solvent, and aqueous sodium hypochlorite to achieve near quantitative conversions, in 72-100% in situ yields, and useful productivities of around 0.05 mol/h with residence times from 3 to 20 minutes. Initial calorimetric studies have been carried out to inform on reaction exotherms, rates and safe operation. Amines which partition mainly in the organic phase require longer reaction times, provided by the CSTR, to compensate for low mass transfer rates in the biphasic system. The green metrics of the reaction have been assessed and compared to existing procedures and have shown the continuous process is improved over previous procedures. The organic solutions of N,N-dialkyl-N-chloramines produced continuously will enable their use in tandem flow reactions with a range of nucleophilic substrates.
- Blacker, A. John,Jolley, Katherine E.
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p. 2408 - 2417
(2016/04/01)
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- Synthesis of ortho -haloaminoarenes by aryne insertion of nitrogen-halide Bonds
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A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of N-X insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.
- Hendrick, Charles E.,Wang, Qiu
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p. 1059 - 1069
(2015/01/30)
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- Transition-metal free umpolung carbon-nitrogen versus carbon-chlorine bond formation
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The formation of carbon-nitrogen (C-N) bonds via an umpolung substitution reaction has been achieved at -78 °C without the need for catalysts, ligands, or additives. The scope is limited to aryl Grignard reagents with N-chloroamines. The findings in this manuscript serve as a reference point for all C-N bond formations involving N-chloroamines and organometallic reagents. Knowing the yields of uncatalyzed reactions will be useful when determining the success of future catalytic methods.
- Sirois, John J.,DeBoef, Brenton
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supporting information
p. 5610 - 5612
(2015/09/21)
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- Iodine-catalyzed efficient amide formation from aldehydes and amines
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An efficient iodine-catalyzed radical oxidative amidation of aldehydes with amines has been developed. This methodology was employed to prepare amides in good to excellent yields with the advantages of wide functional group tolerance and operational simplicity.
- Wang, Peng,Xia, Jiaxuan,Gu, Yueqing
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supporting information
p. 7120 - 7123
(2015/12/01)
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- AIBN-initiated metal free amidation of aldehydes using N-chloroamines
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An efficient and environmentally benign amidation of aldehydes with N-chloroamines has been developed using AIBN as an initiator. This methodology offers a metal free and base free approach and is endowed with mild reaction conditions, high yields, and good functional group tolerance.
- Vanjari, Rajeshwer,Guntreddi, Tirumaleswararao,Singh, Krishna Nand
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supporting information
p. 351 - 356
(2014/01/06)
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- Cobalt-catalyzed electrophilic amination of arylzincs with N-chloroamines
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Roles reversed: An efficient cobalt-catalyzed electrophilic amination of arylzinc reagents has been achieved. A variety of functionalized arylzincs and N-chloroamines were coupled under mild conditions (see scheme). Both secondary and tertiary arylamines were obtained in moderate to excellent yields. Copyright
- Qian, Xin,Yu, Zailu,Auffrant, Audrey,Gosmini, Corinne
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supporting information
p. 6225 - 6229
(2013/07/05)
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- Iron-catalysed oxidative amidation of alcohols with amines
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A new iron-catalysed oxidative amidation of differently substituted benzylic alcohols with mono- and di-substituted amines was developed. The Royal Society of Chemistry 2013.
- Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
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supporting information
p. 3803 - 3807
(2013/07/26)
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- Insertion of arynes into N-halo bonds: A direct approach to O -haloaminoarenes
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A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized aminoarene derivatives.
- Hendrick, Charles E.,McDonald, Stacey L.,Wang, Qiu
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supporting information
p. 3444 - 3447
(2013/07/26)
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- MnO2 promoted sequential C-O and C-N bond formation via C-H activation of methylarenes: A new approach to amides
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A novel and efficient approach for the synthesis of amides has been developed through manganese dioxide promoted nondirected C-H activation of methylarenes under mild reaction conditions employing N-chloroamines as effective coupling partners.
- Vanjari, Rajeshwer,Guntreddi, Tirumaleswararao,Singh, Krishna Nand
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supporting information
p. 4908 - 4911
(2013/10/08)
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- Use of N-chloro-N-methyl-p-toluenesulfonamide in N-chlorination reactions
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Second-order rate constants (k2) were determined for the addition of ten nitrogenous organic compounds (benzylamine, 2,2,2- trifluoethylamine chlorhidrate, methylamine chlorhidrate, glycine ethyl ester chlorhidrate, glycine, glycylglycine chlorhidrate, morpholine, pyperidine, pyperazine and dimethylamine) to the N-chloro-N-methyl-p-toluenesulfonamide (NCNMPT) in the formation reaction of N-chloramines in aqueous solution at 25 °C and ionic strength 0.5 M. The series of nucleophiles considered is structurally very varied and covers five pKa units. The kinetic behaviour is similar for all compounds, being the elementary step the transfer of chlorine from the NCNMPT molecule to the nitrogen of the free amino group. These reactions were found first order in both reagents. The values of the rate constants indicate that the more basic amines produce N-chloramines more readily. Rate constants for the nucleophilic attack are shown to correlate with literature data for some of these nitrogenous organic compounds in their reaction with N-methyl-N-nitroso-p-toluenesulfonamide. Both reactions involve that the rate determining step is the attack of nitrogenous compounds upon electrophilic centre (Cl or else NO group). NCNMPT is a particularly interesting substrate, for which has not hitherto been published kinetic information, that allows us to assess the efficiency and the competitiveness of this reaction and compare it with other agents with a Cl+ atom. Copyright 2013 John Wiley & Sons, Ltd. N-chloro-N-methyl-p-toluensulfonamide is a particularly chlorinating agent. The kinetic behaviour has been studied in the formation reaction of N-chloramines using ten nitrogenous compounds. Copyright
- Pastoriza, Cristina,Antelo, Juan Manuel,Crugeiras, Juan
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supporting information
p. 551 - 559
(2013/07/26)
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- Rh[III]-catalyzed direct C-H amination using N -chloroamines at room temperature
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An efficient Rh(III)-catalyzed direct C-H amination of N-pivaloyloxy benzamides with N-chloroamines proceeding at room temperature was achieved. The versatile directing group allows for selective mono- and diamination and can be readily converted to give valuable benzamide or aminoaniline derivatives. Mechanistic studies have been carried out to elucidate the reaction pathway.
- Grohmann, Christoph,Wang, Honggen,Glorius, Frank
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supporting information; experimental part
p. 656 - 659
(2012/03/08)
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- Rhodium(III)-catalyzed intermolecular direct amination of aromatic C-H bonds with N-chloroamines
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A Rh(III)-catalyzed direct aromatic C-H amination is achieved using N-chloroamines as a reagent. Furthermore, we also developed a one-pot amination protocol involving in situ chlorination of the secondary amines. The catalytic amination operates at mild conditions with excellent functional group tolerance and regioselectivity.
- Ng, Ka-Ho,Zhou, Zhongyuan,Yu, Wing-Yiu
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supporting information; experimental part
p. 272 - 275
(2012/02/04)
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- One-pot synthesis of amides from aldehydes and amines via C-H bond activation
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A one-pot synthesis of amides from aldheydes with N-chloroamines, prepared in situ from amines, has been developed. Both aliphatic and aromatic aldehydes and many types of mono- and disubstituted amines are tolerant in this transformation. This cross-coupling reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents.
- Cadoni, Roberta,Porcheddu, Andrea,Giacomelli, Giampaolo,De Luca, Lidia
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supporting information
p. 5014 - 5017,4
(2012/12/12)
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- One-pot synthesis of amides from aldehydes and amines via C-H bond activation
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A one-pot synthesis of amides from aldheydes with N-chloroamines, prepared in situ from amines, has been developed. Both aliphatic and aromatic aldehydes and many types of mono- and disubstituted amines are tolerant in this transformation. This cross-coupling reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents.
- Cadoni, Roberta,Porcheddu, Andrea,Giacomelli, Giampaolo,De Luca, Lidia
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supporting information
p. 5014 - 5017
(2013/01/15)
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- Copper-catalyzed amination of silyl ketene acetals with N-chloroamines
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A copper(I)/2,2′-bipyridyl complex catalyzes an amination reaction of silyl ketene acetals with N-chloroamines, presenting a new preparative method of α-amino esters.
- Miura, Tomoya,Morimoto, Masao,Murakami, Masahiro
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supporting information
p. 5214 - 5217,4
(2020/09/02)
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- Titanium-mediated amination of Grignard reagents using primary and secondary amines
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Make it, then break it: N-chlorosuccinimide (NCS) was employed as the oxidant in the synthesis of aniline derivatives using the title transformation (see scheme). Functionalization was well tolerated on both the amine and Grignard reagent. An androgen receptor agonist and several analogues were synthesized to demonstrate the utility of this method.
- Barker, Timothy J.,Jarvo, Elizabeth R.
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supporting information; experimental part
p. 8325 - 8328
(2011/10/31)
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- A new entry of amination reagents for heteroaromatic C-H bonds: Copper-catalyzed direct amination of azoles with chloroamines at room temperature
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Chloroamine serves as an efficient amination reagent to the heteroaromatic C-H bond of azole under copper catalysis even at room temperature. This catalysis enables a rapid and concise construction of aminoazoles of great interest in biological and medicinal chemistry.
- Kawano, Tsuyoshi,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; experimental part
p. 6900 - 6901
(2010/07/05)
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- Poly(N,N′-dichloro-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide as novel reagents for the synthesis of N-chloroamines, nitriles and aldehydes
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The applications of poly(N,N′-dichloro-N-ethylbenzene-1,3- disulfonamide) (PCBS) and N,N,N′,N′-tetrachlorobenzene-1,3- disulfonamide (TCBDA) as novel reagents for the preparation of N,N-dichloroamines, nitriles, and aldehydes from primary amines under various conditions are described. Also, a simple and effective procedure for the direct oxidative conversion of primary alcohols into nitriles was successfully carried out with TCBDA and PCBS in aqueous ammonia. Georg Thieme Verlag Stuttgart.
- Ghorbani-Vaghei, Ramin,Veisi, Hojat
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experimental part
p. 945 - 950
(2009/12/01)
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- Umpolung amination: Nickel-catalyzed coupling reactions of N,N-dialkyl-N-chloroamines with diorganozinc reagents
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(Chemical Equation Presented) N,N-Dialkyl-N-chloroamines are an effective source of electrophilic nitrogen for nickel-catalyzed coupling with diarylzinc reagents. A variety of N-chloroamines as well as organozinc reagents react smoothly under the reaction conditions. A one-pot procedure that circumvents the need to isolate the N-chloroamines is described.
- Barker, Timothy J.,Jarvo, Elizabeth R.
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supporting information; experimental part
p. 15598 - 15599
(2010/01/29)
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- Discovery and synthesis of HIV integrase inhibitors: Development of potent and orally bioavailable N-methyl pyrimidones
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The human immunodeficiency virus type-1 (HIV-1) encodes three enzymes essential for viral replication: a reverse transcriptase, a protease, and an integrase. The latter is responsible for the integration of the viral genome into the human genome and, therefore, represents an attractive target for chemotherapeutic intervention against AIDS. A drug based on this mechanism has not yet been approved. Benzyl-dihydroxypyrimidine-carboxamides were discovered in our laboratories as a novel and metabolically stable class of agents that exhibits potent inhibition of the HIV integrase strand transfer step. Further efforts led to very potent compounds based on the structurally related N-Me pyrimidone scaffold. One of the more interesting compounds in this series is the 2-N-Me-morpholino derivative 27a, which shows a CIC95 of 65 nM in the cell in the presence of serum. The compound has favorable pharmacokinetic properties in three preclinical species and shows no liabilities in several counterscreening assays.
- Gardelli, Cristina,Nizi, Emanuela,Muraglia, Ester,Crescenzi, Benedetta,Ferrara, Marco,Orvieto, Federica,Pace, Paola,Pescatore, Giovanna,Poma, Marco,Ferreira, Maria Del Rosario Rico,Scarpelli, Rita,Homnick, Carl F.,Ikemoto, Norihiro,Alfieri, Anna,Verdirame, Maria,Bonelli, Fabio,Paz, Odalys Gonzalez,Taliani, Marina,Monteagudo, Edith,Pesci, Silvia,Laufer, Ralph,Felock, Peter,Stillmock, Kara A.,Hazuda, Daria,Rowley, Michael,Summa, Vincenzo
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p. 4953 - 4975
(2008/03/14)
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- New series of morpholine and 1,4-oxazepane derivatives as dopamine D 4 receptor ligands: Synthesis and 3D-QSAR model
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Since the identification of the dopamine D43 receptor subtype and speculations about its possible involvement in schizophrenia, much work has been put into development of selective D4 ligands. These selective ligands may be effective antipsychotics without extrapyramidal side effects. This work describes the synthesis of a new series of 2,4-disubstituted morpholines and 2,4-disubstituted 1,4-oxazepanes with selectivity for the dopamine D4 receptor. A 3D-QSAR analysis using the GRID/GOLPE methodology was performed with the purpose to get a better understanding of the relationship between chemical structure and biological activity. Inspection of the coefficient plots allowed us to identify that regions which are important for affinity are situated around the two benzene ring systems, a p-chlorobenzyl group, and the aliphatic amine belonging to the morpholine or 1,4-oxazepane system. In addition, the size of the morpholine or 1,4-oxazepane ring seems to be important for affinity.
- Audouze, Karine,Nielsen, Elsebet ?stergaard.,Peters, Dan
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p. 3089 - 3104
(2007/10/03)
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- Structure-activity considerations in kinetics and mechanism of chlorine exchange between chloramine-T and secondary amines
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To study the mechanism of N-chlorination of secondary amines by chloramine-T, the kinetics of the reactions of some aromatic-substituted analogues of N-chlorobenzenesulfonamide with various secondary amines were determined. The importance of amine basicity and reactivity of the N-Cl bond of the N-chlorobenzenesulfonamide was also assessed. The results indicate that a mechanism involving the un-ionized species of both reactants (i.e., a molecular mechanism), rather than an ionic mechanism, is operating and that the reaction most likely proceeds via a six-membered-ring transition state that incorporates a water molecule.
- Dannan,Hussain,Crooks,Dittert
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p. 657 - 660
(2007/10/02)
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- A New Procedure for the Conversion of Thiols into Reactive Sulfenylating Agents
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Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3.Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with β-diketones to afford sulfides.This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise r eactive thiols.
- Barton, D. H. R.,Hesse, R. H.,O'Sullivan, A. C.,Pechet, M. M.
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p. 6697 - 6702
(2007/10/02)
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- HIGH ORTHO-SELECTIVITY IN THE CHLORINATION OF PHENOLS WITH N-CHLORODIALKYLAMINES IN THE PRESENCE OF SILICA.
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Phenols are readily chlorinated by N-chlorodialkylamines in the presence of silica.Furthermore, this approach allows greater selectivity for mono:di and ortho: para chlorination than is possible with many other approaches.
- Smith, Keith,Butters, Michael,Nay, Barry
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p. 1319 - 1322
(2007/10/02)
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- Highly Selective Aromatic Chlorination. Part 1. The 4-Chlorination of Anisole and Phenol with N-Chloroamines in Acidic Solution
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Anisole and phenol are rapidly and efficiently chlorinated by N-chlorodialkylamines and N-chlorotrialkylammonium salts in trifluoracetic acid at room temperature.Product analyses reveal that these reactions have a very marked selectivity for monochlorination of the 4-position.The reactions can also be carried out in aqueous sulphuric acid and under these conditions the selectivity is found to decrease with decreasing acidity of the solvent.The nature of the chlorinating species is discussed and it is proposed that the selective agents in these systems are N-chloroammonium ions.
- Smith, John R. Lindsay,McKeer, Linda C.,Taylor, Jonathan M.
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p. 1533 - 1538
(2007/10/02)
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- Process for preparing N-polythiodimorpholines
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This invention relates to a new process for the preparation of N-polythiodimorpholines wherein morpholine and elemental sulfur in an alcohol mixture are oxidized with an alkali metal hypohalite or an alkaline earth metal hypohalite or N-chloromorpholine to yield N-polythiodimorpholines. The process produces N-polythiodimorpholines without the use of corrosive or toxic chemicals and the product is an economical substitute for conventional rubber curatives.
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- Hypochlorite oxidation of morpholine-borane
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Morpholine-borane reacts with sodium hypochlorite in a 1:4 mole ratio wherein three OCl- species are utilized for hydride oxidation and a fourth is consumed in the chlorination of morpholine. The determination of kinetic parameters, based upon the stopped-flow spectrophotometric measurement of the rate of disappearance of OCl- at 290 nm (pH 9-11), is complicated by these consecutive competitive reactions of hypochlorite. At a given pH, the second-order rate constant for the reaction of OCl- with morpholine is about 103 times greater than that for attack of hypochlorite on amine-borane; thus, a reliable determination of the latter constant was based upon initial rate studies under pseudo-first-order conditions involving a large stoichiometric excess of morpholine-borane. The rate of reaction of hypochlorite with amine-borane is also first order in hydrogen ion and is subject to a normal substrate isotope effect with O(CH2)4NH·BH3 reacting about 1.6 times more rapidly than O(CH2)4NH·BD3. At a given lyonium ion concentration, the reaction is enhanced by a factor of about 3.5 in D2O. It is proposed that the rate-limiting step involves oxidative attack of hypochlorous acid at a boron-hydrogen bond in the amine-borane and that subsequent oxidation of the two remaining hydridic hydrogen atoms is rapid relative to the chlorination of morpholine. The inverse solvent isotope effect is attributed to a higher concentration of DOCl in D2O relative to that of HOCl in normal water at a given pD (pH), but is is likely that this influence is partially offset by a normal secondary isotope effect associated with attack of HOCl (DOCl) at the B-H bond. A four-center activated complex involving the elements O, Cl, B, and H that is formally similar to other transition-state configurations proposed for selected reactions of amine-boranes is considered.
- Wilson, Ian,Kelly, Henry C.
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p. 1622 - 1627
(2008/10/08)
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