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Reinhard Neier - One of the best experts on this subject based on the ideXlab platform.
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Lewis-Acid catalysed tandem reaction Diels–Alder–[3,3] sigmatropic shift between buta-1,3-dienyl Thiocyanic Acid ester and acryloyl chloride: application in the synthesis of 2-azabicyclo[2.2.2]oct-5-ene derivatives
Journal of The Chemical Society Chemical Communications, 1994Co-Authors: Joseph Schoepfer, Christian Marquis, Cécile Pasquier, Reinhard NeierAbstract:Buta-1,3-dienyl Thiocyanic Acid ester reacts with acryloyl chloride in presence of Lewis Acid catalysts to produce directly the rearranged product of type 3bvia a combination of a Diels-Alder reaction with a [3,3] sigmatropic shift; the 1,4-substituted cyclohexene is easily transformed into the 2-azabicyclo[2.2.2]oct-5-ene derivative 6b, which has been used as precursor for the synthesis of the Ibogamin skeleton.
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lewis Acid catalysed tandem reaction diels alder 3 3 sigmatropic shift between buta 1 3 dienyl Thiocyanic Acid ester and acryloyl chloride application in the synthesis of 2 azabicyclo 2 2 2 oct 5 ene derivatives
Journal of The Chemical Society Chemical Communications, 1994Co-Authors: Joseph Schoepfer, Christian Marquis, Cécile Pasquier, Reinhard NeierAbstract:Buta-1,3-dienyl Thiocyanic Acid ester reacts with acryloyl chloride in presence of Lewis Acid catalysts to produce directly the rearranged product of type 3bvia a combination of a Diels-Alder reaction with a [3,3] sigmatropic shift; the 1,4-substituted cyclohexene is easily transformed into the 2-azabicyclo[2.2.2]oct-5-ene derivative 6b, which has been used as precursor for the synthesis of the Ibogamin skeleton.
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the stereochemistry of the 1 4 elimination of Thiocyanic Acid from hex 3 ene 2 5 diyl dithiocyanates
Journal of The Chemical Society Chemical Communications, 1993Co-Authors: Joseph Schoepfer, Eugen Eichenberger, Reinhard NeierAbstract:The elimination of Thiocyanic Acid from the stereoisomers of the hex-3-ene-2,5-diyl dithiocyanates, 4a, 4b, 6a and 6b, in the presence of a strong neutral base in an organic solvent, yields mixtures of the hex-2,4-dien-2-yl thiocyanates 9, 10 and 11via a preferentially syn process.
S Brunken - One of the best experts on this subject based on the ideXlab platform.
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laboratory detection of Thiocyanic Acid hscn
The Astrophysical Journal, 2009Co-Authors: S Brunken, Zhenhong Yu, C A Gottlieb, M C Mccarthy, P ThaddeusAbstract:The rotational spectrum of Thiocyanic Acid HSCN, a highly polar isomer of the well-known astronomical molecule isoThiocyanic Acid HNCS, has been measured in two radio bands: in the centimeter-wave band by Fourier transform microwave spectroscopy in a molecular beam, and in the millimeter-wave band by long-path absorption spectroscopy in a low-pressure glow discharge. Twelve spectroscopic constants were derived from more than 60 a-type rotational transitions between 11 and 346 GHz with J up to 30 and Ka ≤ 6, including seven centimeter-wave transitions with resolved hyperfine structure. With these constants the rotational spectrum in the Ka = 0 and Ka = 1 ladders—those most likely to be observed in space—can now be calculated up to 400 GHz with formal uncertainties of less than 0.2 km s–1 in equivalent radial velocity. Thiocyanic Acid was recently identified in Sgr B2 by Halfen et al. following the laboratory measurements, and there is possible evidence for it in cold dark clouds, with the implication that HSCN may be detectable in many galactic sources.
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detection of a new interstellar molecule Thiocyanic Acid hscn
The Astrophysical Journal, 2009Co-Authors: D T Halfen, S Brunken, C A Gottlieb, M C Mccarthy, Lucy M Ziurys, P ThaddeusAbstract:A new interstellar molecule, HSCN (Thiocyanic Acid), an energetic isomer of the well-known species HNCS, has been detected toward Sgr B2(N) with the Arizona Radio Observatory 12 m telescope. Eight rotational transitions in the Ka = 0 ladder were observed in the 2 mm and 3 mm bands. Five consecutive transitions in the 3 mm band are unblended, but three in the 2 mm band are partially masked by lines of other molecules. The peak intensity of all eight transitions are well described by a rotational temperature that is in very good agreement with that of many other molecules in this source. The line width and radial velocity of HSCN match closely with those of the ground state isomer HNCS (isoThiocyanic Acid), HNCO (isocyanic Acid), and HOCN (cyanic Acid); preliminary maps indicate that all four molecules are similarly distributed in Sgr B2. Although HSCN is calculated to lie over 3000 K higher in energy than HNCS, its column density of 1.3 × 1013 cm–2 in Sgr B2(N) is only three times lower than that of HNCS. The fractional abundances of HSCN and HNCS relative to H2 are 4.5 × 10–12 and 1.1 × 10–11. By analogy with the isomeric pair HCN and HNC, these two sulfur-bearing isomers are plausibly formed from a common cation precursor.
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laboratory and tentative astronomical detection of Thiocyanic Acid hscn
2008Co-Authors: S Brunken, Zhenhong Yu, C A Gottlieb, M C Mccarthy, P Thaddeus, A Belloche, K M MentenAbstract:Author Institution: Harvard Smithsonian Center for Astrophysics and School of Engineering and Applied Sciences, Harvard University, Cambridge, MA 02138; Max-Planck-Institut fur Radioastronomie, 53121 Bonn, Germany
P Thaddeus - One of the best experts on this subject based on the ideXlab platform.
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laboratory detection of Thiocyanic Acid hscn
The Astrophysical Journal, 2009Co-Authors: S Brunken, Zhenhong Yu, C A Gottlieb, M C Mccarthy, P ThaddeusAbstract:The rotational spectrum of Thiocyanic Acid HSCN, a highly polar isomer of the well-known astronomical molecule isoThiocyanic Acid HNCS, has been measured in two radio bands: in the centimeter-wave band by Fourier transform microwave spectroscopy in a molecular beam, and in the millimeter-wave band by long-path absorption spectroscopy in a low-pressure glow discharge. Twelve spectroscopic constants were derived from more than 60 a-type rotational transitions between 11 and 346 GHz with J up to 30 and Ka ≤ 6, including seven centimeter-wave transitions with resolved hyperfine structure. With these constants the rotational spectrum in the Ka = 0 and Ka = 1 ladders—those most likely to be observed in space—can now be calculated up to 400 GHz with formal uncertainties of less than 0.2 km s–1 in equivalent radial velocity. Thiocyanic Acid was recently identified in Sgr B2 by Halfen et al. following the laboratory measurements, and there is possible evidence for it in cold dark clouds, with the implication that HSCN may be detectable in many galactic sources.
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detection of a new interstellar molecule Thiocyanic Acid hscn
The Astrophysical Journal, 2009Co-Authors: D T Halfen, S Brunken, C A Gottlieb, M C Mccarthy, Lucy M Ziurys, P ThaddeusAbstract:A new interstellar molecule, HSCN (Thiocyanic Acid), an energetic isomer of the well-known species HNCS, has been detected toward Sgr B2(N) with the Arizona Radio Observatory 12 m telescope. Eight rotational transitions in the Ka = 0 ladder were observed in the 2 mm and 3 mm bands. Five consecutive transitions in the 3 mm band are unblended, but three in the 2 mm band are partially masked by lines of other molecules. The peak intensity of all eight transitions are well described by a rotational temperature that is in very good agreement with that of many other molecules in this source. The line width and radial velocity of HSCN match closely with those of the ground state isomer HNCS (isoThiocyanic Acid), HNCO (isocyanic Acid), and HOCN (cyanic Acid); preliminary maps indicate that all four molecules are similarly distributed in Sgr B2. Although HSCN is calculated to lie over 3000 K higher in energy than HNCS, its column density of 1.3 × 1013 cm–2 in Sgr B2(N) is only three times lower than that of HNCS. The fractional abundances of HSCN and HNCS relative to H2 are 4.5 × 10–12 and 1.1 × 10–11. By analogy with the isomeric pair HCN and HNC, these two sulfur-bearing isomers are plausibly formed from a common cation precursor.
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laboratory and tentative astronomical detection of Thiocyanic Acid hscn
2008Co-Authors: S Brunken, Zhenhong Yu, C A Gottlieb, M C Mccarthy, P Thaddeus, A Belloche, K M MentenAbstract:Author Institution: Harvard Smithsonian Center for Astrophysics and School of Engineering and Applied Sciences, Harvard University, Cambridge, MA 02138; Max-Planck-Institut fur Radioastronomie, 53121 Bonn, Germany
Arnaud Tatibouët - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and Antimicrobial Evaluation of Oxazole-2(3H)-thione and 2-Alkylsulfanyl-1,3-oxazole Derivatives
Heterocycles, 2020Co-Authors: Sandrina Silva, Patrick Rollin, Amélia P. Rauter, Filipa V.m. Silva, Jorge Justino, Arnaud TatibouëtAbstract:The preparation of oxazole-2(3H)-thiones (OXTs) by condensation of Thiocyanic Acid on α-hydroxycarbonyl substrates has been revisited. Extension to more complex scaffolds afforded chiral OXTs, whereas carbohydrate-fused 2-alkylsulfanyl-1,3-oxazolines led to original hemiaminal structures. A survey of the reactivity of OXTs with various electrophiles showed Sor N-chemoselectivity based on HSAB parameters. Antimicrobial evaluation of selected synthesized compounds was carried out, from which the hemiaminal 15 emerged as a promising antifungal agent. INTRODUCTION Treatment of infectious diseases still represents a topical challenge. The emergent infections as well as the increasing number of multi-drug resistant microbial pathogens specially Gram-positive bacteria have been a serious concern both in hospital and community settings. Linezolid (1) (ZyvoxTM) (Figure 1) is a member of the oxazolidinone drugs active against most Gram-positive pathogens, namely Staphylococcus aureus (MRSA) and Staphylococcus epidermis (MRSE). Although it has been approved HETEROCYCLES, Vol. 88, No. 2, 2014 1013
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N‐Thiocarbonyl Iminosugars: Synthesis and Evaluation of Castanospermine Analogues Bearing Oxazole‐2(3H)‐thione Moieties
European Journal of Organic Chemistry, 2013Co-Authors: Sandrina Silva, Arnaud Tatibouët, Amélia P. Rauter, Elena M. Sánchez-fernández, Carmen Ortiz Mellet, Patrick RollinAbstract:A straightforward and efficient synthetic route to a new class of glycosidase inhibitors containing an oxazole-2(3H)-thione moiety has been devised. The approach involves the formation of α-hydroxy ketones, which, after condensation with Thiocyanic Acid, leads to the formation of the heterocycle. By exploiting the ability of the nitrogen atom of oxazoline-2thione precursors to act as nucleophiles in intramolecular addition, castanospermine analogues could be readily prepared in good overall yields. Glycosidase inhibitory activity com
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HSCN condensation with ulosides: preferred formation of carbohydrate-fused hemiaminals of the 4-hydroxy-1,3-oxazolidine-2-thione type
Tetrahedron Letters, 2008Co-Authors: Sandrina Silva, Ana Catarina Simão, Arnaud Tatibouët, Patrick Rollin, Amélia P. RauterAbstract:Selected ulofuranosides and ulopyranosides react with Thiocyanic Acid to give good yields of stable carbohydrate-fused hemiaminal 1,3-oxazolidine-2-thiones.
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Selective formation of 1,3-oxazolidine-2-thiones on ketohexose templates
Synlett, 2004Co-Authors: Arnaud Tatibouët, Patrick Rollin, Scott P. Lawrence, Geoffrey D. HolmanAbstract:Thiocyanic Acid condensation on selectively protected ketohexose led to the isolation of five out of the seven possible 1,3-oxazolidine-2-thiones (OZT). The four isomeric spiro-OZT synthesized showed promising biological activity against D-fructose transport.
Joseph Schoepfer - One of the best experts on this subject based on the ideXlab platform.
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Lewis-Acid catalysed tandem reaction Diels–Alder–[3,3] sigmatropic shift between buta-1,3-dienyl Thiocyanic Acid ester and acryloyl chloride: application in the synthesis of 2-azabicyclo[2.2.2]oct-5-ene derivatives
Journal of The Chemical Society Chemical Communications, 1994Co-Authors: Joseph Schoepfer, Christian Marquis, Cécile Pasquier, Reinhard NeierAbstract:Buta-1,3-dienyl Thiocyanic Acid ester reacts with acryloyl chloride in presence of Lewis Acid catalysts to produce directly the rearranged product of type 3bvia a combination of a Diels-Alder reaction with a [3,3] sigmatropic shift; the 1,4-substituted cyclohexene is easily transformed into the 2-azabicyclo[2.2.2]oct-5-ene derivative 6b, which has been used as precursor for the synthesis of the Ibogamin skeleton.
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lewis Acid catalysed tandem reaction diels alder 3 3 sigmatropic shift between buta 1 3 dienyl Thiocyanic Acid ester and acryloyl chloride application in the synthesis of 2 azabicyclo 2 2 2 oct 5 ene derivatives
Journal of The Chemical Society Chemical Communications, 1994Co-Authors: Joseph Schoepfer, Christian Marquis, Cécile Pasquier, Reinhard NeierAbstract:Buta-1,3-dienyl Thiocyanic Acid ester reacts with acryloyl chloride in presence of Lewis Acid catalysts to produce directly the rearranged product of type 3bvia a combination of a Diels-Alder reaction with a [3,3] sigmatropic shift; the 1,4-substituted cyclohexene is easily transformed into the 2-azabicyclo[2.2.2]oct-5-ene derivative 6b, which has been used as precursor for the synthesis of the Ibogamin skeleton.
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the stereochemistry of the 1 4 elimination of Thiocyanic Acid from hex 3 ene 2 5 diyl dithiocyanates
Journal of The Chemical Society Chemical Communications, 1993Co-Authors: Joseph Schoepfer, Eugen Eichenberger, Reinhard NeierAbstract:The elimination of Thiocyanic Acid from the stereoisomers of the hex-3-ene-2,5-diyl dithiocyanates, 4a, 4b, 6a and 6b, in the presence of a strong neutral base in an organic solvent, yields mixtures of the hex-2,4-dien-2-yl thiocyanates 9, 10 and 11via a preferentially syn process.