Potential Antiradiation Drugs. II.<sup>1</sup> 2-Amino-1-alkanethiols, 1-Amino-2-alkanethiols, 2-Thiazolines, and 2-Thiazoline-2-thiols<sup>2</sup>

Gr, Handrick; Er, Atkinson; Fe, Granchelli; Rj, Bruni

doi:10.1021/jm00330a008

Cited by 35 publications

(5 citation statements)

References 2 publications

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“…In numerous syntheses the thiazoline heterocycle is obtained from a β-amino alcohol in three steps: acylation of the amino alcohol, thionation of the resulting N -(β-hydroxy)amide into N -(β-hydroxy)thioamide, and intramolecular cyclization (Scheme ). The thionation is generally performed using P 2 S 5 or Lawesson’s reagent (LR). , …”

Section: Syntheses Of 2-thiazolinesmentioning

confidence: 99%

Overview of the Chemistry of 2-Thiazolines

2009

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Section: Syntheses Of 2-thiazolinesmentioning

confidence: 99%

Overview of the Chemistry of 2-Thiazolines

2009

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“…Prepared as described, mp 87−87.5 °C; lit. mp 87.5−88 °C . NMR (CD 3 CN), δ ( J ), 1 H: 6.64, br s, 1H; 4.52 (6.0), t, 1H; 3.45 (5.5), d, 2H; 1.85, s, 3H; 1.21, s, 6H.…”

Section: Methodsmentioning

confidence: 99%

Decomposition of Alkene Adducts of Thianthrene Cation Radical in Nitrile Solvents. Formation of Alkyl-2-oxazolines and a New Class of Four-Component Products: 5-[(1-Alkoxyalkylidene)ammonio]alkylthianthrenium Diperchlorates

et al. 2004

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The monoadducts (4a-d) of thianthrene cation radical perchlorate (1a) and isobutene, 2-methylbutene, 2-methyl-2-butene, and 2-methylpentene decompose spontaneously in acetonitrile (MeCN) solution, with the formation of thianthrene (Th). Decomposition of 4a (1,2-(5,10-thianthreniumdiyl)-2-methylpropane diperchlorate) and 4a', the corresponding dihexafluorophosphate, was studied in depth and extensively with (1)H and (13)C NMR spectroscopy. Decomposition of 4a was found to involve the solvent itself as well as water in the solvent, remaining from incomplete drying, and gave, apart from Th, successively, the perchlorate salts of 2,4,4-trimethyl-2-oxazoline (6) and 2-amino-2-methylpropyl acetate (7). These salts, 6-HClO(4) and 7-HClO(4), respectively, were prepared and used in understanding the reactions of 4a as well as the relationships among 6, 7, and 2-(acetylamino)-2-methyl propanol (8) in acidified MeCN solution. Decompositions of 4a-d in MeCN and other nitriles (RCN) containing an added alcohol (R'OH) led to new products, 5-[(1-alkoxyalkylidene)ammonio]alkylthianthrenium diperchlorates (5a-u). These compounds were identified with (1)H and (13)C NMR spectroscopy and, in part, with X-ray crystallography and elemental analysis. The mechanisms of formation of 5-7 are discussed.

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“…Die benötigten Alaninole (R)-und (S)-2d waren direkt durch Reduktion der entsprechenden Alaninester-Hydrochloride [19] mit Lithiumalanat [20] zugänglich. 2c,e wurden nach N-Acetylierung [21] und Zyklisierung der Amide 5 mit Phosphor(V)-sulfid zu den 4,5-Dihydro-2-methylthiazolen 6 umgesetzt, die in siedender Salzsäure unter Stickstoff 7 c, e lieferten [21]. Über die modifizierte Darstellung und Ermittlung der absoluten Konfiguration von (S)-(+)-7c-HCl haben wir an anderer Stelle berichtet [22], (S)-( + )-7c-HCl wurde mit 11 zu (S)-(-)-10c-2HBr und dem neutralen Di-0-(4-toluoyl)tartrat ( + )-9 umge- …”

Section: Synthese Der Cimetidin-analogen Thioetherunclassified

“…Über Synthese [24], Racemattrennung und absolute Konfiguration [25] des y-Methylderivats von 10a und seine Verwendung als Baustein für die Synthese von Histamin-H 2 -Agonisten [26] haben wir an anderer Stelle berichtet. Der Ersatz der Hydroxylfunktion in 2 durch die Thiolgruppierung nach [21] ist der Konkurrenzmethode [16] bzgl. Praktikabilität und Ausbeute überlegen.…”

Section: Diskussionunclassified

Synthese und absolute Konfiguration kettenverzweigter, Cimetidin-analoger Thioether / Synthesis and Absolute Configuration of Chain Branched Cimetidine Analogous Thioethers

Elza

Dräger

Schunack

1987

Zeitschrift Für Naturforschung B

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Chain branched Cimetidine analogous thioethers, promising building blocks for the preparation of H2-histaminergic compounds, were synthetized from chiral aminoalkanethiols. Enantiomerically pure amino acids or aminoalcohols were used as starting materials. In one case, a resolution via neutral and acid di-O-(4-toluoyl)tartrates was achieved in good yields and satisfying enantiomeric excess. The absolute configuration of an ethyl branched compound was determined using X-ray diffraction and anomalous dispersion

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Potential Antiradiation Drugs. II.¹ 2-Amino-1-alkanethiols, 1-Amino-2-alkanethiols, 2-Thiazolines, and 2-Thiazoline-2-thiols²

Cited by 35 publications

References 2 publications

Overview of the Chemistry of 2-Thiazolines

Overview of the Chemistry of 2-Thiazolines

Decomposition of Alkene Adducts of Thianthrene Cation Radical in Nitrile Solvents. Formation of Alkyl-2-oxazolines and a New Class of Four-Component Products: 5-[(1-Alkoxyalkylidene)ammonio]alkylthianthrenium Diperchlorates

Synthese und absolute Konfiguration kettenverzweigter, Cimetidin-analoger Thioether / Synthesis and Absolute Configuration of Chain Branched Cimetidine Analogous Thioethers

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Potential Antiradiation Drugs. II.1 2-Amino-1-alkanethiols, 1-Amino-2-alkanethiols, 2-Thiazolines, and 2-Thiazoline-2-thiols2

Cited by 35 publications

References 2 publications

Overview of the Chemistry of 2-Thiazolines

Overview of the Chemistry of 2-Thiazolines

Decomposition of Alkene Adducts of Thianthrene Cation Radical in Nitrile Solvents. Formation of Alkyl-2-oxazolines and a New Class of Four-Component Products: 5-[(1-Alkoxyalkylidene)ammonio]alkylthianthrenium Diperchlorates

Synthese und absolute Konfiguration kettenverzweigter, Cimetidin-analoger Thioether / Synthesis and Absolute Configuration of Chain Branched Cimetidine Analogous Thioethers

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Potential Antiradiation Drugs. II.¹ 2-Amino-1-alkanethiols, 1-Amino-2-alkanethiols, 2-Thiazolines, and 2-Thiazoline-2-thiols²