- Completion of the Set: Synthesis of the (6,X′)-Flubromazepam Positional Isomers as Standards for Forensic Analysis
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Mounting concern among forensic examiners regarding the emergence of positional isomers as technically legal alternatives to scheduled benzodiazepines has encouraged the preemptive synthesis of analogues as standards. Recently, flubromazepam was identified by the Drug Enforcement Administration for future scheduling, and subsequently, 9 of the 12 possible flubromazepam isomers were synthesized. However, the three (6,X′)-isomers proved inaccessible via that approach. Herein, through a redesigned synthetic approach, the remaining three isomers were obtained, thus completing the set and enabling future forensic analysis.
- Parker, Ariel N.,France, Stefan
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p. 813 - 822
(2021/12/27)
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- Camptothecin derivative as well as preparation method and application thereof
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The invention discloses a camptothecin derivative shown as a formula (I). The synthetic method of the derivative comprises the following steps: carrying out a radical substitution reaction on a compound (II) to produce a compound (III) under light conditions; carrying out a coupled reaction on the compound (III) and a boronic acid derivative R-B(OH)2 (IV) to produce a compound (V); carrying out areduction reaction on the compound (V) to produce a compound (VI) under the effect of a catalyst palladium on carbon; and carrying out a Friedlander condensation reaction on the compound (VI) and tricyclic ketolide (VII), thereby obtaining the camptothecin derivative (I). The synthetic method disclosed by the invention is mild in reaction conditions, high in reaction efficiency, low in cost, highin yield and excellent in product quality, has less three-waste pollution in the reaction and is suitable for industrial production. The prepared camptothecin derivative can be applied to preparing antitumor drugs. The structural formula is as shown in the description.
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Paragraph 0047; 0048; 0049
(2018/09/20)
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- Reexamination of the bromination of 2-nitrobenzaldehyde with NBS or NaBr-NaIO4 in sulfuric acid
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Two literature procedures for selective bromination of 2-nitrobenzaldehyde using N-bromosuccinimide (NBS) or NaBr-NaIO4 in sulfuric acid were examined. In contrast to the reports that 4-bromo-2-nitrobenzaldehyde is formed as a single product in good yield, reactions using NBS gave a number of isomeric mono- and dibrominated products identified by spectroscopical methods and by sodium borohydride reduction to the corresponding benzyl alcohol, and reactions using NaBr-NaIO4 did not furnish any product. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Cummings, Matthew M.,Soederberg, Bjoern C. G.
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supporting information
p. 954 - 958
(2014/03/21)
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- METHOD FOR MAKING BIARYL COMPOUNDS, COMPOUNDS MADE BY THE METHOD, AND METHOD FOR THEIR USE
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Certain disclosed embodiments of the present invention concern a method for making biaryl compounds by combining a diene with a dienophile under reaction conditions that facilitate a Diels-Alder reaction. Certain embodiments are particularly directed to making a tetra-ortho-substituted biaryl compounds. The disclosed method may involve using novel dienes, dienophiles, or both. Similarly, certain of the biaryl compounds are novel compounds too. Additional disclosed embodiments concern a method for making useful compounds by first making a Diels-Alder adduct. The Diels-Alder adduct is then further modified or coupled to other compounds. The method can be used to make carbazoles, such as Siamenol. Disclosed biaryl compounds are useful for a number of applications, such as pharmacophores and organocatalysts.
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Page/Page column 58; 66; 120
(2009/01/23)
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- Synthesis of tetra-ortho-substituted, phosphorus-containing and carbonyl-containing biaryls utilizing a Diels-Alder approach
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The application of the Diels-Alder approach to biaryls (DAB) is described for the synthesis of tetra-ortho-substituted biaryl compounds containing orthogonally functionalized substituents. The syntheses of phosphorus- containing, disubstituted alkynes and
- Ashburn, Bradley O.,Carter, Rich G.,Zakharov, Lev N.
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p. 9109 - 9116
(2008/02/09)
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- Diels-Alder approach to polysubstituted biaryls: Rapid entry to tri- and tetra-ortho-substituted phosphorus-containing biaryls
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Rapid construction: A Diels-Alder-based approach to the synthesis of highly functionalized biaryls from readily available precursors is disclosed. The utility of these biaryl templates in palladium-mediated couplings is explored along with subsequent redu
- Ashburn, Bradley O.,Carter, Rich G.
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p. 6737 - 6741
(2007/10/03)
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- FIBROSIS INHIBITOR
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Medicament being useful as a fibrosis inhibitor for organs or tissues, which comprises a compound of the formula (I): wherein Ring Z is optionally substituted pyrrole ring, etc.; W2 is -CO-, -SO2-, optionally substituted C1-C4 alkylene, etc.; Ar2 is optionally substituted aryl, etc.; W1 and Ar1 mean the following (1) and (2):(1) W1 is optionally substituted C1-C4 alkylene, etc.; Ar1 is optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms:(2) W1 is optionally substituted C2-C5 alkylene, optionally substituted C2-C5 alkenylene, etc.; and Ar1 is aryl or monocyclic heteroaryl, which is substituted by carboxyl, alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof.
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- Pyrrole derivatives
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Pyrrole derivatives represented by the following formula: wherein Ring Z is an optionally substituted pyrrole ring, etc.; W2 is —CO—, —SO2—, an optionally substituted C1-C4 alkylene, etc.; Ar2 is an optionally substituted aryl, etc.; W2 and Ar1 mean the following (1) and (2): (1) W1 is an optionally substituted C1-C4 alkylene, etc.; Ar1 is an optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms: (2) W1 is an optionally substituted C2-C5 alkylene, an optionally substituted C2-C5 alkenylene, etc.; and Ar1 is an aryl or monocyclic heteroaryl, which are substituted by carboxyl, an alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof These compounds are useful as medicaments such as a fibrosis inhibitor for organs or tissues.
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- Design of triple helix forming C-glycoside molecules
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The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2′-deoxynucleotide residues are reported. The 2-aminoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of
- Li, Jian-Sen,Fan, Yun-Hua,Zhang, Yi,Marky, Luis A.,Gold, Barry
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p. 2084 - 2093
(2007/10/03)
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- Polyaza heterocycles. Part 3. Halogenation of 1-substituted quinoxalinocinnolines: mechanistic implications
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Since it has been proposed that halogenation of quinoxalinocinnolines at C-10, using hydrogen chloride or bromide in chloroform, occurs through initial protonation of the substrate at N-12, attempts have been made to inhibit this protonation by the introduction of an additional substituent at C-1.Where this substituent is chloro, bromo or methyl, chlorination still occurs preferentially at C-10, although the yield and the reaction rate decrease along the series, lending weight to the mechanistic proposal.
- Harvey, Ian W.,Smith, David M.,White, Charles R.
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p. 1699 - 1704
(2007/10/03)
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- Acid-catalysed Cyclisation of o-Sulphonamido Ketene Dithioacetal S-Oxides: A Novel Synthesis of the Indole Ring System
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Treatment of o-sulphonamido aryl ketene dithioacetal S-oxides with hydrochloric acid in the presence of hydrogen sulphide gives 2-methylthioindoles.
- Hewson, Alan T.,Hughes, Kevin,Richardson, Steward K.,Sharpe, David A.,Wadsworth, Alan H.
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p. 1565 - 1569
(2007/10/02)
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