- Electrochemical access to benzimidazolone and quinazolinone derivatives: Via in situ generation of isocyanates
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Isocyanates are the key intermediates for several organic transformations towards the synthesis of diverse pharmaceutical targets. Herein, we report the development of an oxidant-free protocol for electrochemical in situ generation of isocyanates. This strategy highlights expedient access to benzimidazolones and quinazolinones and eliminates the need for exogenous oxidants. Furthermore, detailed mechanistic studies provide strong support towards our hypothesis of in situ isocyanate generation. This journal is
- Saha, Debarshi,Taily, Irshad Maajid,Naik, Sumitra,Banerjee, Prabal
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p. 631 - 634
(2021/01/29)
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- Structure-activity relationships of natural quinone vegfrecine analogs with potent activity against VEGFR-1 and -2 tyrosine kinases
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A series of analogs of vegfrecine, a natural quinone vascular endothelial growth factor receptor (VEGFR) tyrosine kinase inhibitor, was synthesized via oxidative amination of 2,5-dihydroxybenzamide with functionalized arylamine followed by ammonolysis and
- Adachi, Hayamitsu,Nosaka, Chisato,Atsumi, Sonoko,Nakae, Koichi,Umezawa, Yoji,Sawa, Ryuichi,Kubota, Yumiko,Nakane, Chie,Shibuya, Masabumi,Nishimura, Yoshio
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p. 734 - 742
(2021/07/25)
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- Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis
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A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 percent yield and with up to >99.5 percent ee, and follow-up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.
- Chen, Shuming,Han, Feng,Houk, K. N.,Ivlev, Sergei,Meggers, Eric,Xie, Xiulan,Ye, Chen-Xi
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supporting information
p. 13552 - 13556
(2020/06/05)
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- Synthetic studies toward isoschizogamine: Construction of pentacyclic core structure
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Development of a concise construction of the pentacyclic core skeleton of isoschizogamine was described. Tetracyclic A,B,D,F-rings structure was assembled by intramolecular aza-Diels–Alder reaction via an ortho-iminoquinone methide intermediate. The C-ring was formed by oxidation of the benzylic position with a combination of Cr(CO)6 and t-BuOOH, followed by the introduction of an aminoethyl side chain, C–H oxidation of the lactam ring with CrO3 and n-Bu4NI, and final cyclization to construct the cyclic aminal moiety.
- Sugimoto, Kenji,Fujiwara, Hiroaki,Takada, Akihiro,Kim, Dong-Gil,Ueda, Hirofumi,Tokuyama, Hidetoshi
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p. 1028 - 1049
(2019/07/31)
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- Structurally Diverse Mitochondrial Branched Chain Aminotransferase (BCATm) Leads with Varying Binding Modes Identified by Fragment Screening
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Inhibitors of mitochondrial branched chain aminotransferase (BCATm), identified using fragment screening, are described. This was carried out using a combination of STD-NMR, thermal melt (Tm), and biochemical assays to identify compounds that b
- Borthwick, Jennifer A.,Ancellin, Nicolas,Bertrand, Sophie M.,Bingham, Ryan P.,Carter, Paul S.,Chung, Chun-Wa,Churcher, Ian,Dodic, Nerina,Fournier, Charlène,Francis, Peter L.,Hobbs, Andrew,Jamieson, Craig,Pickett, Stephen D.,Smith, Sarah E.,Somers, Donald O'N.,Spitzfaden, Claus,Suckling, Colin J.,Young, Robert J.
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p. 2452 - 2467
(2016/04/10)
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- Extending the stetter reaction with 1,6-acceptors
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Pace Stetter: A new N-heterocyclic carbene (NHC)-catalysed transformation is described-the intramolecular vinylogous Stetter reaction. This transformation can be effected with both thiazolium and triazolium-based catalysts, using aromatic and aliphatic aldehydes, employing α,β,γ,δ- unsaturated esters, ketones, phosphonates and N-acylpyrroles, and can be conducted enantioselectively (see scheme). Copyright
- Law, Katherine R.,McErlean, Christopher S. P.
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supporting information
p. 15852 - 15855
(2014/04/03)
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- Synthesis of a small library of non-symmetric cyclic sulfamide HIV-1 protease inhibitors
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A set of 11 non-symmetric cyclic sulfamide HIV-1 protease inhibitors were synthesized and evaluated. The use of a key microwave-assisted silver(I) oxide mediated selective mono N-benzylation reaction enabled fast and straightforward synthesis. The Ki
- Ax, Anna,Joshi, Advait A.,Orrling, Kristina M.,Vrang, Lotta,Samuelsson, Bertil,Hallberg, Anders,Karlén, Anders,Larhed, Mats
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experimental part
p. 4049 - 4056
(2010/07/09)
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- Nitrile oxide 1,3-dipolar cycloadditions in water: Novel isoxazoline and cyclophane synthesis
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Facile examples of one-pot 1,3-dipolar cycloadditions in water are described to generate novel benzopyran, quinoline and cyclophane isoxazolines. Georg Thieme Verlag Stuttgart.
- Bala, Kason,Hailes, Helen C.
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p. 3423 - 3427
(2007/10/03)
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- Investigation into the structure-activity relationship of novel concentration dependent, dual action T-type calcium channel agonists/antagonists
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This paper describes the synthesis and biological evaluation of a series of straight chain analogs of a compound (1) that was previously synthesized in our research program. These compounds, which are T-type calcium channel antagonists, exhibits potent anti-proliferative activity against a variety of cancer cells. A structure-activity relationship of these analogs against a variety of cancer cells has provided insight into a logical pharmacophore for this series of compounds. Furthermore, this series of compounds has presented itself as a set of novel, concentration dependent, dual action agonists/antagonists for the T-type calcium channel.
- McCalmont, William F.,Patterson, Jaclyn R.,Lindenmuth, Michael A.,Heady, Tiffany N.,Haverstick, Doris M.,Gray, Lloyd S.,Macdonald, Timothy L.
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p. 3821 - 3839
(2007/10/03)
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- Chiral Acetals as Stereoinductors: Diastereoface Selective Alkylation of Dihydrobenzoxazine-Derived Amide Enolates
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Novel dihydrobenzoxazine-derived acetals of type 3 have been developed for asymmetric C-alkylations of propionyl amide enolates. High stereoselectivities are obtained for amides 15 and 22 which are rationalized in terms of intramolecular metal chelate formation.
- Mulzer, Johann,Langer, Oliver,Hiersemann, Martin,Bats, Jan W.,Buschmann, Juergen,Luger, Peter
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p. 6540 - 6546
(2007/10/03)
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