cas 5713-61-1, THIOPHEN-2-YL-MAGNESIUM BROMIDE 1.0M

Articles about 5713-61-1Total 24 be found

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Vanishing microwave effects: Influence of heterogeneity
A consistent setup of experiments has been conducted to demonstrate an enhanced reaction rate under microwave irradiation as compared to conventional heating, i.e. a real microwave effect It was found that addition of a cosolvent, diminishing the heterogeneous character of the reaction mixture, greatly reduced the microwave effect. This was demonstrated by two examples; selective mono-urea formation and racemization of an N-acetylamino acid. Furthermore, formation of a Grignard reagent was accelerated under MW irradiation by electrostatic etching of the metal surface. The microwave effect observed in these reactions seems to rely on heterogeneity and specific interactions on the solid-liquid interface. Basic understanding of these findings is crucial for scaling up microwave assisted processes.
Dressen, Mark H. C. L.,Van De Kruijs, Bastiaan H. P.,Meuldijk, Jan,Vekemans, Jef A. J. M.,Hulshof, Lumbertus A.
p. 865 - 869
(2007)
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Effects of conjugated bridges on the photovoltaic properties of: Ortho -functionalized perylene diimides for non-fullerene polymer solar cells
Perylene diimide (PDI) derivatives have great potential to replace the commonly used fullerene derivatives in bulk heterojunction (BHJ) polymer solar cells (PSCs). However, PDI-based molecules have a strong tendency to aggregate in thin films, which prevents the formation of appropriate phase separation. To alleviate this problem, much effort has been devoted to developing twisted PDI dimers with functional bridges at bay positions. Unfortunately, the bay-functionalized PDI dimers exhibit relatively low electron mobilities due to the excessive twist geometry. To solve this dilemma, an efficient method is to functionalize the PDI at less sterically-encumbered ortho-positions. In this article, we synthesized two novel ortho-functionalized PDI dimers, namely PDI-2Th-PDI and PDI-ThFTh-PDI, and investigated the influence of the conjugated bridge length on the physical and photovoltaic properties of PDIs. After introducing a fluorene bridge between the thiophene units, PDI-ThFTh-PDI with the extended conjugate length possessed a relatively low-crystalline nature and therefore exhibited one order of magnitude lower electron mobility compared to PDI-2Th-PDI. As a result, the power conversion efficiency (PCE) of solar cells fabricated with PDI-2Th-PDI as the electron acceptor and PTB7-Th as the electron donor is almost twice that of the solar cell with PDI-ThFTh-PDI as the acceptor. Our findings provide important guidelines for the design of more efficient ortho-functionalized PDI acceptors.
Wu, Jiazun,Li, Xiangchun,Liu, Xiaodong,Wu, Shuanghong,Lai, Wen-Yong,Zheng, Yonghao
p. 13171 - 13178
(2018)
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Stereodivergent Construction of Vicinal Acyclic Quaternary-Tertiary Carbon Stereocenters by Michael-Type Alkylation of α,α-Disubstituted N- tert-Butanesulfinyl Ketimines
Vicinal quaternary-tertiary carbon stereocenters were constructed with excellent stereoselectivity via aza-enolization of enantioenriched acyclic N-tert-butanesulfinyl ketimines bearing two sterically similar α-linear alkyl substituents followed by conjugate addition to nitroalkenes. Further changes of the absolute configuration of the sulfinyl group and/or the α-stereocenter in the ketimine allowed the facile stereodivergent synthesis of all four diastereomers of the Michael-type alkylation adducts. This reaction is a successful example of acyclic stereocontrol based on stereoselective α-deprotonation for the formation of fully substituted aza-enolates from ketone derivatives.
Liu, Hui,Lu, Chong-Dao,Yao, Yun,Yisimayili, Nuermaimaiti
supporting information
p. 7450 - 7455
(2021/10/02)

Scalable Continuous Synthesis of Grignard Reagents from in Situ-Activated Magnesium Metal
The continuous synthesis of Grignard reagents has been investigated under continuous processing conditions using Mg turnings at variable liquid throughputs and concentrations. A novel process window easily accessible through continuous processing was employed, namely, using a large molar access of Mg turnings within the reactor and achieving Mg activation by mechanical means. A laboratory and a 10-fold-increased pilot-scale reactor setup were built and evaluated, including integrated inline analytics via ATR-IR measurements. The main goal of this work was to explore the full potential of classic Grignard reagent formation through the use of scalable flow chemistry and to allow for fast and safe process optimization. It was found that on both the laboratory and pilot scales, full conversion of the employed halides could be achieved with a single passage through the reactor. Furthermore, Grignard reagent yields of 89-100% were reached on the laboratory scale.
Deitmann, Eva,G?ssl, Lars,Hofmann, Christian,L?b, Patrick,Menges-Flanagan, Gabriele
p. 315 - 321
(2020/03/10)

Palladium-catalyzed aerobic oxidative double allylic C-H oxygenation of alkenes: A novel and straightforward route to α,β-unsaturated esters
A mild tandem oxidative functionalization of allyl aromatic hydrocarbons was accomplished using the catalytic system of Pd(OAc)2/DMA under 1 atm O2. The green twofold C-O bond formation involving double allylic C-H oxygenation unlocks opportunities for markedly different synthetic strategies. Moreover, the reaction affords aryl α,β-unsaturated esters directly from readily available terminal olefins in moderate to good yields with excellent chemo- and stereoselectivities.
Yang, Wanfei,Chen, Huoji,Li, Jianxiao,Li, Chunsheng,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 9575 - 9578
(2015/06/08)

Selective introducing of aryl and amino groups: Reaction of benzanthrone and organometallic reagents
The reaction of benzanthrone and aryl magnesium bromides produced 6-aryl-substituted benzanthrones in moderate to good yields. Similarly, 6-alkylaminobenzanthrones were selectively prepared by the reaction of benzanthrone and lithium alkylamides. In contrast, for the lithium arylamides, the arylamino groups were selectively introduced at the 4-position of the benzanthrone.
Umeda, Rui,Namba, Teruaki,Yoshimura, Tomohiro,Nakatsukasa, Masamichi,Nishiyama, Yutaka
p. 1526 - 1531
(2013/02/23)

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY
The present invention relates to compounds acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists, to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmaceutical active ingredients.
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Page/Page column 69; 70

(2013/02/27)

Manufacturing process for tiotropium bromide
The present invention relates to a novel manufacturing process of pharmaceutically active compound of formula I used as a long-acting anticholinergic bronchodilator. Starting from oxalic acid derivative of formula III the invention describes preparation of a novel cyclic anhydride of formula II which is very efficient precursor in the synthesis of Tiotropium bromide (compound of formula I).
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(2012/05/21)

Copper-catalyzed difluoromethylation of β,γ-unsaturated carboxylic acids: An efficient allylic difluoromethylation
Not one but two! A new strategy for the regiospecific construction of compounds with allylic CF2H groups has been developed. The decarboxylative (phenylsulfonyl)difluoromethylation of β,γ- unsaturated carboxylic acids is catalyzed by a Lewis acid (CuCl 2·2 H2O), and the resulting product easily undergoes desulfonylation. Copyright
He, Zhengbiao,Hu, Mingyou,Luo, Tao,Li, Lingchun,Hu, Jinbo
supporting information
p. 11545 - 11547
(2013/01/15)

N-(3-(IMIDAZO [1,5-A]PYRIMIDIN-4-YL)PHENYL]-SULFONAMIDES AND N-[3-(IMIDAZO[1,5-A]PYRIMIDIN-4-YL)-PHENYL]-CARBOXAMIDES AND THEIR USE AS GABAA RECEPTOR MODULATORS
The present invention relates to compounds of formula I wherein R1, R2, R3 and X are as defined in the claims. The compounds have specific affinity for the GABAA receptor and are therefore useful in the treatment and prevention of diseases modulated by the 1 and 2-GABAA receptors.
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(2008/06/13)

Arylzinc species by microwave assisted Grignard formation-transmetallation sequence: Application in the Negishi coupling
Arylmagnesium species can be efficiently generated from magnesium turnings and aryl chlorides or aryl bromides under dielectric heating conditions. Subsequent microwave assisted transmetallation using ZnCl2-TMEDA afforded the corresponding arylzinc reagents. A sequential microwave assisted arylmagnesium formation-transmetallation-Negishi coupling protocol suitable for automated multiple parallel synthesis has been developed.
Mutule, Ilga,Suna, Edgars
p. 11168 - 11176
(2007/10/03)

2-ARYLOXYETHYL GLYCINE DERIVATIVES AND THEIR USE AS GLYCINE TRANSPORT INHIBITORS
The present invention relates to certain 2-aryloxyethyl glycine derivatives that exhibit activity as inhibitors of the glycine type-1 transporter, to pharmaceutical compositions containing them and to their use in the treatment of neurological and neuropsychiatric disorder.
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(2010/02/14)

THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS
Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).
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Page 317

(2008/06/13)

Quinuclidine derivatives and their use as muscarinic M3 receptor ligands
A compound according to formula (I) wherein: is a phenyl ring, a C4 to C9 heteroaromatic compound containing one or more heteroatoms, or a naphthalenyl, 5,6,7,8-tetrahydronaphthalenyl or biphenyl group; R1, R2 and R3 each independently represent a hydrogen or halogen atom, or a hydroxy group, or a phenyl, —OR4, —SR4, —NR4R5, —NHCOR4, —CONR4R5, —CN, —NO2, —COOR4 or —CF3 group, or a straight or branched lower alkyl group which may optionally be substituted, for example, with a hydroxy or alcoxy group, wherein R4 and R5 each independently represent a hydrogen atom, straight or branched lower alkyl group, or together form an alicyclic ring; or R1 and R2 together form an aromatic, alicyclic or heterocyclic ring; n is an integer from 0 to 4; A represents a —CH2—, —CH═CR6, —CR6=CH—, —CR6R7—, —CO—, —O—, —S—, —S(O)—, SO2 or —NR6— group, wherein R6 and R7 each independently represent a hydrogen atom, straight or branched lower alkyl group, or R6 and R7 together form an alicyclic ring; m is an integer from 0 to 8; provided that when m=0, A is not —CH2—; p is an integer from 1 to 2 and the substitution in the azoniabicyclic ring may be in the 2, 3 or 4 position including all possible configurations of the asymmetric carbons; B represents a group of formula i) or ii): wherein R10 represents a hydrogen atom, a hydroxy or methyl group; and R8 and R9 each independently represents wherein R11 represents a hydrogen or halogen atom, or a straight or branched lower alkyl group and Q represents a single bond, —CH2—, —CH2—CH2—, —O—, —O—CH2—, —S—, —S—CH2— or —CH═CH—, and when i) or ii) contain a chiral centre they may represent either configuration; X represents a pharmaceutically acceptable anion of a mono or polyvalent acid, which shows high affinity for muscarinic M3 receptors (Hm3).
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(2008/06/13)

Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same
The invention concerns novel phenylcyclidine derivatives with selective affinity for low affinity receptors, methods for preparing them, pharmaceutical compositions containing them and their use as protective agents for central or peripheral nervous system cells against acute or chronic degeneration, or as an anticonvulsant.
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(2008/06/13)

NMR studies on derivatives of heteroaromatic compounds: Exceptionally small carbon-carbon couplings, 1JCC, in 2-lithiothiophene, 2-lithio-N-methylpyrrole and 2-lithiofuran
Spin-spin carbon-carbon coupling constants across one bond and carbon-proton coupling constants across one, two and three bonds have been measured for a large series of derivatives of five-membered heterocyclic compounds. This included 2-methyl and 2-lithio derivatives of furan, N-methyl pyrrole and thiophene and a series of 2-R-substituted thiophenes where R = O-t-Bu, Cl, Br, I, Si(CH3)3, MgBr and MgTh. For the long-range C-H couplings their signs have been determined in several compounds by the use of modern 2D NMR techniques, and in all the cases they have been found to be positive. A good linear dependence upon electronegativity of the substituent has been observed for 1JCC, 2JC2H3 and 3JC2H4. Very small 1JCC couplings of ca. 30 Hz only have been found in all three lithio compounds; they belong to the smallest couplings of this type reported up to now. They are accompanied by very large and positive two-bond couplings, 2JC2H3 of ca. +20 Hz, which in turn are the largest couplings of this type reported so far. In both cases the changes observed are interpreted in terms of the changes in the Fermi contact contribution.
Dabrowski, Andrzej,Kamienska-Trela, Krystyna,Wojcik, Jacek
p. 91 - 102
(2007/10/03)

Medicinal thiophene compounds
A method of treating tumor including administering to a subject an effective amount of a compound of the following formula: STR1 wherein m is 1-4; and each of A and B, independently, is H, C1-7 alkyl, C2-7 alkenyl, C2-7 alkynyl, (CH2)n CHO, (CH2)o COOH, C1-7 alkoxy, C2-7 alkoxyalkyl, C1-7 hydroxyalkyl, CN, NO2, halogen, CH(OR1)2, CO.R1, NR2 R3 or its acid salt, CO.NR2 R3, CHR1 NR2 R3 or its acid salt, CH=NR2, C CR4, CR1 =CR5 R6, CO.CH=CHR7, CH=CHR8, or COOR9 ; in which each of n and o, independently, is 0-4; R1 is C1-4 alkyl or C1-4 acyl; each of R2 and R3, independently, is H, C1-4 alkyl, or C1-4 hydroxyalkyl; R4 is H, C1-4 alkyl, C2-4 alkenyl, COR2, COOR10, C1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C1-4 dihydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C1-4 halogenated alkyl; OR1, or NHR7 ; each of R5 and R6, independently, is H, CHO, COR1, COOH, COOR9, CN, or halogen; R7 is H, C1-4 alkyl, 2-thienyl, phenyl, mono-substituted phenyl, or di-substituted phenyl; R8 is COOR2, CO.CHO, C1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether; and R9 is H, C1-4 alkyl, phenyl, mono-substituted phenyl, di-substituted phenyl, or 2-thienyl.
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(2008/06/13)

Medicinal thiophene compounds
A method of augmenting the immune system including administering to a subject an effective amount of a compound of the following formula: STR1 wherein m is 1-4; and each of A and B, independently, is H, C1-7 alkyl, C2-7 alkenyl, C2-7 alkynyl, (CH2)n CHO, (CH2)o COOH, C1-7 alkoxy, C2-7 alkoxyalkyl, C1-7 hydroxyalkyl, CN, NO2, halogen, CH(OR1)2, CO.R1, NR2 R3 or its acid salt, CO.NR2 R3, CHR1 NR2 R3 or its acid salt, CH=NR2, C CR4, CR1 =CR5 R6, CO.CH=CHR7, CH=CHR8, or COOR9 ; in which each of n and o, independently, is 0-4; R1 is C1-4 alkyl or C1-4 acyl; each of R2 and R3, independently, is H, C1-4 alkyl, or C1-4 hydroxyalkyl; R4 is H, C1-4 alkyl, C2-4 alkenyl, COR2, COOR10, C1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C1-4 dihydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C1-4 halogenated alkyl; OR1, or NHR7 ; each of R5 and R6, independently, is H, CHO, COR1, COOH, COOR9, CN, or halogen; R7 is H, C1-4 alkyl, 2-thienyl, phenyl, mono-substituted phenyl, or di-substituted phenyl; R8 is COOR2, CO.CHO, C1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether; and R9 is H, C1-4 alkyl, phenyl, mono-substituted phenyl, di-substituted phenyl, or 2-thienyl.
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(2008/06/13)

Medicinal thiophene compounds
A method of treating inflammation including administering to a subject an effective amount of a compound of the following formula: STR1 wherein m is 1-4; and each of A and B, independently, is H, C1-7 alkyl, C2-7 alkenyl, C2-7 alkynyl, (CH2)n CHO, (CH2)o COOH, C1-7 alkoxy, C2-7 alkoxyalkyl, C1-7 hydroxyalkyl, CN, NO2, halogen, CH(OR1)2, CO.R1, NR2 R3 or its acid salt, CO.NR2 R3, CHR1 NR2 R3 or its acid salt, CH=NR2, C CR4, CR1 =CR5 R6, CO.CH=CHR7, CH=CHR8, or COOR9 ; in which each of n and o, independently, is 0-4; R1 is C1-4 alkyl or C1-4 acyl; each of R2 and R3, independently is H, C1-4 alkyl, or C1-4 hydroxyalkyl; R4 is H, C1-4 alkyl, C2-4 alkenyl, COR2, COOR10, C1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C1-4 dihydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C1-4 halogenated alkyl; OR1, NHR7 ; each of R5 R6, independently, is H, CHO, COR1, COOH, COOR9, CN, or halogen; R7 is H, C1-4 alkyl, 2-thienyl, phenyl, mono-substituted phenyl, or di-substituted phenyl; R8 is COOR2, CO.CHO, C1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether; and R9 is H, C1-4 alkyl, phenyl, mono-substituted phenyl, di-substituted phenyl, or 2 -thienyl.
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(2008/06/13)

Synthesis and monoamine oxidase B catalyzed oxidation of C-4 heteroaromatic substituted 1,2,3,6-tetrahydropyridine derivatives
The monoamine oxidase B (MAO-B) catalyzed oxidation of amines has been proposed to proceed via a polar pathway, an initial single-electron transfer pathway and an initial hydrogen atom transfer pathway. Results from previous studies on selected N-cyclopropyl-4-substituted-1,2,3,6-tetrahydropyridine derivatives have led us to consider a mechanism for these cyclic tertiary allylamines which may not necessarily involve the aminyl radical cation as required by an initial single-electron transfer step. The studies summarized in this paper were undertaken to explore further the structural features that determine the MAO-B substrate and/or inactivator properties of various 1,4-disubstituted tetrahydropyridine derivatives. We report here the results of our studies on the synthesis and MAO-B catalyzed oxidation of 1-methyl- and 1-cyclopropyl-1,2,3,6-tetrahydropyridine derivatives bearing a variety of heteroaromatic groups at C-4. All of the N-cyclopropyltetrahydropyridine analogs were time and concentration dependent inhibitors of MAO-B while all of the N-methyltetrahydropyridine analogs and the N-cyclopropyl-4-(1- methyl-2-pyrryl)tetrahydropyridine analog were substrates. The substrate properties (k(cat)/K(M)) covered a range of 6 to 1800 min-1 mM-1 while the range for the inactivator properties for which k(inact)/K(I) values could be obtained was 0.1-1.0 min-1 mM-1. The partition ratios for the N-cyclopropyl analogs varied from 4 to 17 except for the 4-(1-methyl-2- pyrryl) analog, which had a partition ratio of 400. These results are discussed in terms of the putative allylic radical intermediate and in the context of the hydrogen atom transfer and single-electron transfer based mechanisms.
Nimkar, Sandeep K.,Anderson, Andrea H.,Rimoldi, John M.,Stanton, Matthew,Castagnoli, Kay P.,Mabic, Stephane,Wang,Castagnoli Jr., Neal
p. 1013 - 1022
(2007/10/03)

Selective synthesis of α-substituted oligothiophenes
An improved synthesis of selectively mono- and dibrominated oligothiophenes using the system N-bromosuccinimide/dimethylformamide is reported together with the preparation of the corresponding α-alkyl and α,α-dialkyl derivatives which represent potent biologically active agents.
Bauerle,Wurthner,Gotz,Effenberger
p. 1099 - 1103
(2007/10/02)

AN EFFICIENT ROUTE TO HETEROARENE-SUBSTITUTED VINYL- AND ALLYL-SILANES VIA PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING
Heteroarene-substituted vinyl- and allyl-silanes were obtained in good yields by the cross-coupling reaction of either heteroaryl Grignard reagents with halovinyl- and haloallyl-silanes or, alternatively, silyl- and silylmethyl-substituted vinylmetallic reagents with heteroaryl halides in the presence of PdCl2(dppb) as a catalyst.
Minato, Akio,Suzuki, Keizo
p. 83 - 86
(2007/10/02)

Reaction of 2,3,4-Trichlorothiopene and Tetrachlorothiophene with Ethylmagnesium Bromide. Preparation of Trichloro-2-thienylmagnesium Bromide and 2,5-Bis(Bromomagnesium)-3,4-Dichlorothiophene
Metal-hydrogen exchange between ethylmagnesium bromide and 2,3,4-trichlorothiophene in THF gives trichloro-2-thienylmagnesium bromide in at least 86percent yield.Similarly, metal-halogen exchange between tetrachlorothiophene and ethylmagnesium bromide produces trichloro-2-thienylmagnesium bromide in 84percent yield.The reaction of two and a half equivalents of ethylmagnesium bromide with 2,3,4-trichlorothiophene yields a mixture of trichloro-2-thienylmagnesium bromide (40percent) and 2,5-bis(Bromomagnesium)-3,4-dichlorothiophene (41percent).The Grignard reagents were characterised by converting them into the corresponding known trimethylsilylderivatives and carboxylic acids.
Rahman, M. T.
p. 21 - 23
(2007/10/02)

Anti-spasmodic substituted quinolizidine and indolizidine compounds
Phenyl- or thienyl-substituted quinolizidines and indolizidines as well as quaternary salts thereof are disclosed. These compounds are useful as pharmaceutical agents exhibiting strong spasmolytic, anti-ulcer, anti-histaminic and antiemetic activities with minimized side effects such as thirst and dilation of the pupil. Phenyl- or thienyl-substituted quinolizidine-methanols and indolizidine-methanols which are starting materials of the aforementioned quinolizidine and indolizidine compounds are also useful as having spasmolytic, anti-ulcer, anti-histaminic and anti-emetic activities.
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(2008/06/13)