- Synthesis and reactions of silylcarbamates with bulky substituents
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New silylcarbamates containing bulky substituents were synthesized in order to study their reactivity with nucleophilic agents as lactones and chloroformates.We suggest a mechanism for these reactions.Key words: Silicon
- Moertl, M.,Knausz, D.,Kolos, Zs.,Szakacs, L.,Csakvari, B.
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- The synthesis of phenyl carbamates catalyzed by iron (II) bromide: An oxidative approach for cross-coupling of phenols with formamides
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The carbamate group is a key structural motif in many approved drugs and pro-drugs. There is increasing use of carbamates in the medicinal chemistry and agrochemical industry. We present, reagents and chemical methodologies for the synthesis of carbamates, and recent applications. The direct coupling of simple phenols with mono- and di-alkyl formamides provided the phenylcarbamate products.
- Adurthi, Suryakumari,Sudhakar, Chithaluri,Vala, Manoj Kumar,Vanam, Shekhar
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- Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement
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Herein, we report that iron(II)/ammonium persulfate in aqueous acetonitrile mediates the Newman-Kwart rearrangement of O-aryl carbamothioates. Electron-rich substrates react rapidly under moderate heating to afford the rearranged products in excellent yie
- Gendron, Thibault,Pereira, Raul,Abdi, Hafsa Y.,Witney, Timothy H.,?rstad, Erik
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p. 274 - 278
(2020/01/02)
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- Synthesizing method of multi-aryl substituted naphthol derivate
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The invention discloses a synthesizing method of a multi-aryl substituted naphthol derivate. The method comprises the following steps: performing cyclization reaction on a phenol derivate and a diaromatic acetylene derivate in an organic solvent under the
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Paragraph 0033; 0034; 0035; 0036
(2017/12/27)
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- Pd(II) catalyzed ortho C-H iodination of phenylcarbamates at room temperature using cyclic hypervalent iodine reagents
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A novel approach to access ortho iodinated phenols using cyclic hypervalent iodine reagents through palladium(II) catalyzed C-H activation has been developed through weak coordination. The reaction showed excellent regioselectivity, reactivity and good functional group tolerance. A unique mechanism was proposed.
- Sun, Xiuyun,Yao, Xia,Zhang, Chao,Rao, Yu
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supporting information
p. 10014 - 10017
(2015/06/22)
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- Ligand-assisted copper-catalyzed oxidative cross-coupling of simple phenols with formamides for the synthesis of carbamates
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An oxidative approach for the synthesis of phenyl carbamates has been achieved by ligand-assisted copper-catalyzed cross-dehydrogenative coupling (CDC) of phenols with formamides. The direct coupling of simple phenols with mono- and dialkyl formamides pro
- Reddy, Nagireddy Veera,Kumar, Gadde Sathish,Kumar, Pailla Santhosh,Kantam, M. Lakshmi,Reddy, Kallu Rajender
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supporting information
p. 2133 - 2138
(2014/11/08)
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- Room-temperature Pd-catalyzed C-H chlorination by weak coordination: One-pot synthesis of 2-chlorophenols with excellent regioselectivity
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A room-temperature Pd(ii)-catalyzed regioselective chlorination reaction has been developed for a facile one-pot synthesis of a broad range of 2-chlorophenols. The reaction demonstrates an excellent regioselectivity and reactivity for C-H chlorination. This reaction represents one of the rare examples of mild C-H functionalization at ambient temperature.
- Sun, Xiuyun,Sun, Yonghui,Zhang, Chao,Rao, Yu
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supporting information
p. 1262 - 1264
(2014/02/14)
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- A general approach towards catechol and pyrogallol through ruthenium- and palladium-catalyzed C-H hydroxylation by weak coordination
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An efficient ruthenium(II)- and palladium(II)-catalyzed C-H hydroxylation of aryl carbamates has been developed for the facile synthesis of catechols and pyrogallols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by a gram-scale synthesis.
- Yang, Xinglin,Sun, Yonghui,Chen, Zhang,Rao, Yu
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supporting information
p. 1625 - 1630
(2014/06/09)
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- A copper metal-organic framework as an efficient and recyclable catalyst for the oxidative cross-dehydrogenative coupling of phenols and formamides
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A crystalline porous metal-organic framework Cu2(BPDC)2(BPY) (BPDC=4,4'-biphenyldicarboxylate, BPY=4,4'-bipyridine) was synthesized and characterized by several techniques including XRD, SEM, TEM, thermogravimetric analysis, FTIR, atomic absorption spectrophotometry, hydrogen temperature-programmed reduction, and nitrogen physisorption measurements. The Cu2(BPDC)2(BPY) could be employed as a heterogeneous catalyst for the copper-catalyzed cross-dehydrogenative coupling reaction of DMF with 2-substituted phenols to form organic carbamates through CH activation under oxidative conditions. The Cu2(BPDC)2(BPY) offered higher catalytic activity than common copper salts such as Cu(OAc)2, CuCl, CuCl2, CuI, and Cu(NO3)2 as well as other Cu-MOFs such as Cu3(BTC)2, Cu(BDC), and Cu(BPDC). The Cu2(BPDC)2(BPY) catalyst could be facilely separated from the reaction mixture, could be recovered and reused several times without significant degradation in catalytic activity.
- Phan, Nam T.S.,Nguyen, Tung T.,Vu, Phuong H. L.
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p. 3068 - 3077
(2013/10/21)
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- Palladium catalyzed C-H functionalization of O-arylcarbamates: Selective ortho -bromination using NBS
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A series of cyclometalated palladium complexes derived from O-phenylcarbamates has been synthesized by the reaction of the respective carbamates with Pd(OAc)2 in the presence of acids, CF 3CO2H, CF3SO3/sub
- John, Alex,Nicholas, Kenneth M.
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experimental part
p. 5600 - 5605
(2012/07/30)
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- Rhodium-catalyzed selective C-H activation/olefination of phenol carbamates
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Rh(III)-catalyzed ortho C-H activation/olefination of phenol carbamates has been developed. High regioselectivity is observed with a range of phenol carbamates enabling efficient coupling with acrylates and styrenes. This reaction exhibits different react
- Gong, Tian-Jun,Xiao, Bin,Liu, Zhao-Jing,Wan, Jian,Xu, Jun,Luo, Dong-Fen,Fu, Yao,Liu, Lei
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supporting information; experimental part
p. 3235 - 3237
(2011/08/22)
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- Anionic ortho-fries rearrangement, a facile route to arenol-based mannich bases
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Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90 C, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino)methyl]-8- hydroxy-1-naphthaldehydes is presented.
- Assimomytis, Nikos,Sariyannis, Yiannis,Stavropoulos, Georgios,Tsoungas, Petros G.,Varvounis, George,Cordopatis, Paul
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scheme or table
p. 2777 - 2782
(2010/03/03)
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- Suppressing the anionic fries rearrangement of aryl dialkylcarbamates; the isolation of a crystalline ortho-deprotonated carbamate
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In the presence of organolithium bases phenyl dialkylcarbamates have previously been shown to undergo facile rearrangement to yield the corresponding salicylamides. However, heterometallic lithium diethyl(2,2,6,6- tetramethylpiperidido)zincate achieves th
- Garcia, Felipe,McPartlin, Mary,Morey, James V.,Nobuto, Daisuke,Kondo, Yoshinori,Naka, Hiroshi,Uchiyama, Masanobu,Wheatley, Andrew E. H.
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p. 644 - 647
(2008/09/17)
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- AZAARENE DERIVATIVES
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A compound represented by the general formula: wherein X1 represents a nitrogen atom or a group represented by the formula -CR10=; X2 represents a nitrogen atom or a group represented by the formula -CR11=; Y represents an oxygen atom or the like; R1 represents a C1-6 alkoxy group, an optionally substituted C6-10 aryloxy group, a group represented by the formula -NR12aR12b or the like; R2 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, or the like; R3, R4, R5, R6, R7, R8, R10 and R11 each independently represent a hydrogen atom, a halogen atom, an optionally substituted C1-6 alkyl group, or the like; R9 represents a group represented by the formula -NR16aR16b or the like; and R12a, R12b, R16a and R16b each independently represent a hydrogen atom, an optionally substituted C1-6 alkyl group, or the like, a salt thereof, or a hydrate of the foregoing.
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Page/Page column 93
(2008/06/13)
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- Potassium fluoride on alumina: Synthesis of O-aryl N,N-dimethylthiocarbamates and their rearrangement into S-aryl N,N-dimethylthiocarbamates under microwave irradiation
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A series of O-aryl N,N-dimethyl thiocarbamates have been prepared by the reaction of dimethylthiocarbamoyl chloride with phenols absorbed on potassium fluoride on alumina. The rearrangement of O-aryl N,N-dimethylthiocarbamate into S-aryl N,N-dimethylthiocarbamate under microwave irradiation was also studied. The use of conductive support like graphite or silicon carbide allow these rearrangements although the O-aryl N,N-dimethylthiocarbamates have very low dielectric lost.
- Villemin, Didier,Hachemi, Messaoud,Lalaoui, Mekki
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p. 2461 - 2471
(2007/10/03)
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- Contra-thermodynamic trans-esteripication of carbamates by counter-attack strategy: A viable non-phosgene, non-mic route to carbamate pesticides
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Treatment of methyl N-methylcarbaaate (1, R= Me) with phosphorus oxychloride and 1-naphthol results in the formation of the transesterified product, 1-naphthyl N-methylcarbamate (2, Ar=1-naphthy 1) in good yield. Similarly, ethyl N-methylthiocarbamate (5) is converted to 1-naphthyl N-methylcarbamate (2, Ar= 1-naphthyl) on treatment with phosphorus oxychloride and 1-naphthol. The mechanism of these interesting and industrially important transformations is discussed.
- Kulkarni,Naik,Tandel,Rajappa
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p. 1249 - 1256
(2007/10/02)
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- Cycloaddition in synthesis of sulfonamide derivatives. IV. One-pot synthesis of 3-dimethylamino-4,1,2-benzoxathiazine 1,1-dioxides, 3-methoxy-4-methyl-1,2,4-benzothiadiazine 1,1-dioxide and 3-dimethylamino-1,4,2-benzodithiazine 1,1-dioxides
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A novel, one-pot synthesis of 3-dimethylamino-4,1,2-benzoxathiazine 1,1-dioxides (7), 3-methoxy-4-methyl-1,2,4-benzothiadiazine 1,1-dioxide (9) and 3-dimethylamino-1,4,2-benzodithiazine 1,1-dioxides (11) is described. The procedure in the case of 7 involv
- Iwakawa,Tamura,Murabayashi,Hayase
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p. 1939 - 1943
(2007/10/02)
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- Infrared Spectra and Transmission of Electronic Effects in Substituted Phenyl N,N-Dimethylcarbamates and S-Phenyl N,N-Dimethylthiocarbamates
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Carbonyl stretching frequencies in CCl4 and CHCl3 and hydroxyl stretching frequency shifts of phenol as a proton donor in CCl4 were measured for series of substituted phenyl N,N-dimethylcarbamates (I) and S-phenyl N,N-dimethylthiocarbamates (II).The data
- Perjessy, Alexander,Jones, Ronald G.,McClair, Susan L.,Wilkins, Joyce M.
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p. 1266 - 1271
(2007/10/02)
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