The Experts below are selected from a list of 267 Experts worldwide ranked by ideXlab platform
Junliang Zhang - One of the best experts on this subject based on the ideXlab platform.
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reaction of two differently functionalized oxiranes with nickel perchlorate a modular entry to highly substituted 1 3 dioxolanes
ChemInform, 2014Co-Authors: Zuliang Chen, Yuanjing Xiao, Junliang ZhangAbstract:An alternative route for the synthesis of the title compounds by using oxiranes instead of aldehydes is presented via sequential Meinwald Rearrangement and cycloaddition.
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reaction of two differently functionalized oxiranes with nickel perchlorate a modular entry to highly substituted 1 3 dioxolanes
European Journal of Organic Chemistry, 2013Co-Authors: Zuliang Chen, Yuanjing Xiao, Junliang ZhangAbstract:Nickel perchlorate catalyzed sequential Meinwald Rearrangement of a terminal oxirane through C–O bond cleavage, and cycloaddition with a donor–acceptor oxirane through C–C bond cleavage was developed. The same catalyst mediates the ring opening of the oxirane moiety in two different ways. This method provides an alternative route to synthesize highly substituted 1,3-dioxolanes by using oxiranes instead of aldehydes.
Matthias Otte - One of the best experts on this subject based on the ideXlab platform.
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The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination.
Organic letters, 2016Co-Authors: Martine R. Tiddens, Robertus J. M. Klein Gebbink, Matthias OtteAbstract:A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald Rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald Rearrangement-reductive amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields.
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The B(C6F5)3‑Catalyzed Tandem Meinwald Rearrangement–Reductive Amination
2016Co-Authors: Martine R. Tiddens, Robertus J. M. Klein Gebbink, Matthias OtteAbstract:A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald Rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald Rearrangement–reductive amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields
Prabal Banerjee - One of the best experts on this subject based on the ideXlab platform.
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lewis acid catalysed tandem Meinwald Rearrangement intermolecular 3 2 cycloaddition of epoxides with donor acceptor cyclopropanes synthesis of functionalized tetrahydrofurans
European Journal of Organic Chemistry, 2015Co-Authors: Ashok Kumar Pandey, Asit Ghosh, Prabal BanerjeeAbstract:A Lewis-acid-catalysed tandem Meinwald Rearrangement/[3+2]-cycloaddition of epoxides with donor–acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation was achieved using an InCl3–PyBOX catalyst system.
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Lewis‐Acid‐Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]‐Cycloaddition of Epoxides with Donor–Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans
European Journal of Organic Chemistry, 2015Co-Authors: Ashok Kumar Pandey, Asit Ghosh, Prabal BanerjeeAbstract:A Lewis-acid-catalysed tandem Meinwald Rearrangement/[3+2]-cycloaddition of epoxides with donor–acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation was achieved using an InCl3–PyBOX catalyst system.
Jas S Ward - One of the best experts on this subject based on the ideXlab platform.
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total syntheses of the resorcylic acid lactone neocosmosin a and its enantiomer
Journal of Organic Chemistry, 2015Co-Authors: Yiwen Zhang, Michael Dlugosch, Martin Jubermann, Martin G Banwell, Jas S WardAbstract:A total synthesis of the structure, 1, assigned to the recently reported resorcylic acid lactone (RAL) neocosmosin A has been established. Olefin-cross metathesis, ring-closing metathesis, palladium-catalyzed Meinwald Rearrangement, and Mitsunobu esterification reactions were used as key steps. A late-stage and simple modification to the reaction sequence also provided compound ent-1 that, in fact, represents the true structure of the natural product.
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Total Syntheses of the Resorcylic Acid Lactone Neocosmosin A and Its Enantiomer
2015Co-Authors: Yiwen Zhang, Michael Dlugosch, Martin G Banwell, Martin Jübermann, Jas S WardAbstract:A total synthesis of the structure, 1, assigned to the recently reported resorcylic acid lactone (RAL) neocosmosin A has been established. Olefin-cross metathesis, ring-closing metathesis, palladium-catalyzed Meinwald Rearrangement, and Mitsunobu esterification reactions were used as key steps. A late-stage and simple modification to the reaction sequence also provided compound ent-1 that, in fact, represents the true structure of the natural product
Vera L. Mamedova - One of the best experts on this subject based on the ideXlab platform.
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Acid-Catalyzed Rearrangements of 3-Aryloxirane-2-Carboxamides: Novel DFT Mechanistic Insights.
ChemistryOpen, 2020Co-Authors: Hui Zhu, Vakhid A. Mamedov, Vera L. Mamedova, Sergey A. Katsyuba, Stefan GrimmeAbstract:Efficient synthesis of 3-arylquinolin-2(1H)-ones and N-(2-carboxyaryl)-oxalamides from protic acid-catalyzed Rearrangements of 3-aryloxirane-2-carboxamides was achieved recently but not well understood. In contrast to the classical Meinwald Rearrangement, extensive DFT calculations reveal that the proximal aryl and amide groups have strong synergetic effects to control the amide-aided and aryl-directed oxirane-opening and further Rearrangement sequences. The ortho-nitro substituent of the proximal aryl is directly involved in a nucleophilic oxirane ring-opening, the amide C=O is an important proton shuttle for facile H-shifts, while the N-aryl may act as a potential ring-closing site via Friedel-Crafts alkylation. The mechanistic insights are useful for rational design of novel synthesis by changing the aryl and amide functional groups proximal to the oxirane ring.
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The Meinwald Rearrangement in tandem processes (microreview)
Chemistry of Heterocyclic Compounds, 2017Co-Authors: Vera L. Mamedova, Gul'naz Z. KhikmatovaAbstract:The Meinwald Rearrangement refers to the process of conversion of epoxides to carbonyl compounds, accompanied by the migration of one of the substituents of the epoxide ring. In this microreview, literature concerning the Meinwald Rearrangement in tandem processes from 2012 to the present is surveyed. Tandem processes in this review are interpreted as one-pot processes that represent a set of reactions taking place without changing the conditions during the experiment.
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Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-yl)(aryl)methanones (o-nitrobenzalacetophenone oxides)
Tetrahedron, 2017Co-Authors: Vakhid A. Mamedov, Vera L. Mamedova, Gul'naz Z. Khikmatova, Ildar Kh. Rizvanov, Victor V. Syakaev, Dmitry E. Korshin, Ekaterina V. Mironova, Olga B. Bazanova, Shamil K. LatypovAbstract:Abstract An efficient sodium dithionite (Na2S2O4)-mediated method for construction of 3-hydroxyquinolines via in situ Meinwald Rearrangement/intramolecular reductive cyclization of o-nitrobenzalacetophenone oxides has been developed. The practical approach is of excellent functional group compatibility with as high as 98% yield under mild reaction conditions. Moreover, further manipulation successfully furnished 4-bromo substituted derivatives which may provide a promising potential application in exploring biologically active analogs of 3-hydroxyquinolines.
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A novel acid-catalyzed Rearrangement of 2-substituted-3-(2-nitrophenyl)oxiranes for the synthesis of di- and mono-oxalamides
RSC Advances, 2016Co-Authors: Vakhid A. Mamedov, Vera L. Mamedova, Gul'naz Z. Khikmatova, Ildar Kh. Rizvanov, Ekaterina V. Mironova, Olga B. Bazanova, Dmitry B. Krivolapov, Denis V. Chachkov, Sergey A. Katsyuba, Shamil K. LatypovAbstract:A novel one-pot synthetic approach to N1-(2-carboxyaryl)-N2-(aryl or H)oxalamides from 3-(2-nitroaryl)oxirane-2-carboxamides via the classical Meinwald Rearrangement and a new Rearrangement sequence has been developed. The methodology is applicable to the synthesis of N-(2-carboxyphenyl)aryloxalmonoamides from (3-(2-nitrophenyl)oxiran-2-yl)(aryl)methanones. The method is operationally simple and high yielding, thus providing a new useful formula for both anthranilic acid derivatives and oxalamides.
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Metal-Free Intramolecular Transannulation of N,3-Diaryloxirane-2-carboxamides: A Concise and Versatile Route to 3-Arylquinolin-2(1H)-ones.
ChemInform, 2015Co-Authors: Vakhid A. Mamedov, Vera L. Mamedova, Saniya F. Kadyrova, Gul'naz Z. Khikmatova, Aidar T. Gubaidullin, Ildar Kh. Rizvanov, Shamil K. LatypovAbstract:The intramolecular transannulation of trans-epoxides (III) towards quinolinones (IV) proceeds via a Meinwald Rearrangement and Friedel—Crafts alkylation processes, featuring an exclusive 1,2-aryl migration.
