KI-catalyzed synthesis of S-Thiocarbamates by cross-coupling of cyclohexyl isocyanide with sulfonyl chlorides

A simple and efficient process for direct generation of various S-thiocarbamates is developed by cross-coupling of readily available sulfonyl chlorides with cyclohexyl isocyanide. The yields are excellent and the structures of the generated S-thiocarbamates are characterized by nuclear magnetic resonance spectroscopy, infrared spectroscopy, and high-resolution mass spectrometry together with X-ray crystallographic analysis. The protocol has the advantages of using easily available reagents, employs inexpensive KI as the reagent, demonstrates good functional group tolerance, and utilizes mild reaction conditions.

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Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Marine Drugs ◽

10.3390/md20010051 ◽

2022 ◽

Vol 20 (1) ◽

pp. 51

Author(s):

Senhua Chen ◽

Heng Guo ◽

Minghua Jiang ◽

Qilin Wu ◽

Jing Li ◽

...

Keyword(s):

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Crystallographic Analysis ◽

Selective Cytotoxicity ◽

X Ray ◽

Planar Structures ◽

Spectroscopic Analyses ◽

Ic50 Values ◽

Anti Inflammatory ◽

Resolution Mass

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

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Synthesis of spiro[benzo[4,5]imidazo[2,1-b][1,3]thiazole-2,3-thiolane]s via sulfa-Michael/aldol cascade reactions

Journal of Chemical Research ◽

10.1177/1747519819831898 ◽

2019 ◽

Vol 43 (1-2) ◽

pp. 63-66 ◽

Cited By ~ 1

Author(s):

Jiaying Lei ◽

Xinliang Fu ◽

Yulin Huang ◽

Xiaofang Li

Keyword(s):

Mass Spectrometry ◽

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

Cascade Reactions ◽

Cascade Reaction ◽

Crystallographic Analysis ◽

X Ray ◽

Resolution Mass

The sulfa-Michael/aldol cascade reaction of ( Z)-2-arylmethylidene-benzo[4,5]imidazo[2,1- b]thiazol-3(2H)-ones and 1,4-dithiane-2,5-diol afforded novel 2-aryl-4-hydroxy-spiro[benzo[4,5]imidazo[2,1- b][1,3]thiazole-2,3-thiolan]-3-ones in moderate yields. The structures of all the products were characterized thoroughly by nuclear magnetic resonance, infrared and high-resolution mass spectrometry together with X-ray crystallographic analysis.

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Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

Synthesis ◽

10.1055/s-0036-1591925 ◽

2018 ◽

Vol 50 (10) ◽

pp. 2009-2018

Author(s):

Jan-Hendrik Lamm ◽

Philipp Niermeier ◽

Leif Körte ◽

Beate Neumann ◽

Hans-Georg Stammler ◽

...

Keyword(s):

Mass Spectrometry ◽

Building Block ◽

High Resolution Mass Spectrometry ◽

Cross Coupling ◽

Easy Access ◽

Coupling Reactions ◽

X Ray Diffraction ◽

X Ray ◽

Cross Coupling Reactions ◽

Resolution Mass

An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9H)-one was reacted with ethynylmagnesium bromide in the presence of CeCl3; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.

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Synthesis of 1,2,3-triazole-substituted 6,7-dihydroindolizin-8(5H)-one derivatives mediated by Selectfluor

Journal of Chemical Research ◽

10.1177/1747519819857478 ◽

2019 ◽

Vol 43 (5-6) ◽

pp. 179-183

Author(s):

Yulin Huang ◽

Jiaying Lei ◽

Xinliang Fu ◽

Wenlin Xie ◽

Xiaofang Li

Keyword(s):

Mass Spectrometry ◽

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

Crystallographic Analysis ◽

X Ray ◽

High Resolution Mass ◽

Moderate Yield ◽

Resolution Mass

The 1,2,3-triazole and 1 H-1,2,3-benzotriazole-substituted 6,7-dihydroindolizin-8(5 H)-one derivatives were synthesized by the reaction of ( E)-7-(arylmethylidene)-6,7-dihydroindolizin-8(5 H)-ones with 1,2,3-triazole and 1 H-1,2,3-benzotriazole in the presence of Selectfluor in moderate yield. The structures of all the products were characterized thoroughly by nuclear magnetic resonance, infrared, and high-resolution mass spectrometry together with X-ray crystallographic analysis.

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N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine

Molbank ◽

10.3390/m1181 ◽

2021 ◽

Vol 2021 (1) ◽

pp. M1181

Author(s):

Valentin Wydra ◽

Stefan Gerstenecker ◽

Dieter Schollmeyer ◽

Stanislav Andreev ◽

Teodor Dimitrov ◽

...

Keyword(s):

Title Compound ◽

High Resolution Mass Spectrometry ◽

Nucleophilic Aromatic Substitution ◽

Resonance Spectroscopy ◽

Aromatic Substitution ◽

X Ray Diffraction ◽

Inhibitory Potency ◽

X Ray ◽

Step Procedure ◽

Resolution Mass

Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6Kβ/S6K2).

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Synthesis of 2-(1-Oxo-2,3-Dihydro-1H-Pyrrolizin-2-yl)-2-(Aryl)Acetonitrile Derivatives Via Michael Addition of Trimethylsilyl Cyanide

Journal of Chemical Research ◽

10.3184/174751918x15357145868004 ◽

2018 ◽

Vol 42 (9) ◽

pp. 467-470 ◽

Cited By ~ 1

Author(s):

Demin Ren ◽

Jiaying Lei ◽

Xianyong Yu ◽

Yulin Huang ◽

Xiaofang Li

Keyword(s):

Mass Spectrometry ◽

High Resolution ◽

Michael Addition ◽

High Resolution Mass Spectrometry ◽

Crystallographic Analysis ◽

X Ray ◽

Trimethylsilyl Cyanide ◽

Tetrabutylammonium Fluoride ◽

High Resolution Mass ◽

Resolution Mass

Several 2-aryl-2-(1-oxo-2,3-dihydro-1 H-pyrrolizin-2-yl)acetonitrile derivatives were synthesised by Michael addition of ( E)-2-arylidene-2,3-dihydro-1 H-pyrrolizin-1-ones with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride in moderate yields. The structures of all of the products were fully characterised by NMR, IR and high-resolution mass spectrometry, together with X-ray crystallographic analysis.

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Triple aldose reductase/α-glucosidase/radical scavenging high-resolution profiling combined with high-performance liquid chromatography–high-resolution mass spectrometry–solid-phase extraction–nuclear magnetic resonance spectroscopy for identification of antidiabetic constituents in crude extract of Radix Scutellariae

Journal of Chromatography A ◽

10.1016/j.chroma.2015.07.010 ◽

2015 ◽

Vol 1408 ◽

pp. 125-132 ◽

Cited By ~ 33

Author(s):

Yousof Tahtah ◽

Kenneth T. Kongstad ◽

Sileshi G. Wubshet ◽

Nils T. Nyberg ◽

Louise H. Jønsson ◽

...

Keyword(s):

Mass Spectrometry ◽

High Resolution ◽

High Performance ◽

High Resolution Mass Spectrometry ◽

Solid Phase ◽

Radical Scavenging ◽

Resonance Spectroscopy ◽

Phase Extraction ◽

Radix Scutellariae ◽

Resolution Mass

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ANALYSIS OF SOLDERS ON TIN AND LEAD BASES BY X-RAY FLOORESCENT SPECTROSCOPY

Proceedings of VIAM ◽

10.18577/2307-6046-2021-0-4-124-131 ◽

2021 ◽

pp. 124-131

Author(s):

A.V. Alekseev ◽

◽

G.V. Orlov ◽

P.S. Petrov ◽

A.V. Slavin ◽

...

Keyword(s):

Emission Spectroscopy ◽

High Resolution Mass Spectrometry ◽

Analytical Signal ◽

Atomic Emission ◽

Standard Samples ◽

X Ray ◽

Fundamental Parameters ◽

The Matrix ◽

Resolution Mass

The determination of the elements Cu, Ni, Sb, Bi, Pb, Zn and Fe in the tin-based solder VPr35, as well as the elements Sn, Ni, Sb, Bi and In in the lead-based VPr40 solder by the method of х-ray fluorescence spectroscopy has been carried out. The calibration dependences are corrected taking into account the superposition of signals from interfering elements on the analytical signal and changes in intensity caused by inter-element influences in the matrix. The analysis was carried out by the method of fundamental parameters without using standard samples. The correctness of the results obtained was confirmed by their comparative analysis by atomic emission spectroscopy and high-resolution mass spectrometry with a glow discharge.

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The Meisenheimer rearrangement in heterocyclic synthesis. II. Synthesis and X-ray crystal structure of a tetrahydro-1H-2,3-benzoxazocine and preparation of a hexahydro-2,3-benzoxazonine

Australian Journal of Chemistry ◽

10.1071/ch9801323 ◽

1980 ◽

Vol 33 (6) ◽

pp. 1323 ◽

Cited By ~ 15

Author(s):

JB Bremner ◽

EJ Browne ◽

PE Davies ◽

CLWAH Raston

Keyword(s):

Molecular Structure ◽

Crystal Structure ◽

Acetic Acid ◽

Crystal And Molecular Structure ◽

Phosphorus Oxychloride ◽

Crystallographic Analysis ◽

Heterocyclic Synthesis ◽

Reaction Conditions ◽

X Ray ◽

Heterocyclic Derivatives

The heterocyclic derivatives, 8,9-dimethoxy-3-methyl-1-phenyl-3,4,5,6- tetrahydro-1H-2,3-benzoxazocine(3a) and 9,10-dimethoxy-3-methyl-1- phenyl-1,3,4,5,6,7-hexahydro-2,3-benzoxazonine (3b),examples of two new ring systems, have been prepared by Meisenheimer rearrangement of the corresponding 2-benzazepine and 2-benzazocine N-oxide derivatives (2a) and (2b). The Bischler-Napieralski-type cyclization reaction was used in the preparation of the tertiary amine precursors of these N-oxides reaction conditions for the cyclization were critical and phosphorus oxychloride in refluxing butanenitrile was found to give the best yields of the seven- or eight-membered cyclic imine intermediates. Reductive cleavage of the benzoxazocine derivative (3a) with zinc in acetic acid followed by N-methylation gave the expected product, [2-{3- (dimethylamino)propyl}-4,5-di-methoxyphenyl]phenylmethanol (12). The crystal and molecular structure of (3a) has been determined by X-ray crystallographic analysis.

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