Tosyl

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Min Shi - One of the best experts on this subject based on the ideXlab platform.

Yunyun Liu - One of the best experts on this subject based on the ideXlab platform.

Julian P Henschke - One of the best experts on this subject based on the ideXlab platform.

Zhen Yang - One of the best experts on this subject based on the ideXlab platform.

Anatoly D Shutalev - One of the best experts on this subject based on the ideXlab platform.

  • synthesis of functionalized pyridine derivatives by an amidoalkylation staudinger aza wittig sequence
    Tetrahedron Letters, 2012
    Co-Authors: Anastasia A Fesenko, Anatoly D Shutalev
    Abstract:

    Abstract A new efficient methodology for the preparation of 3,4-difunctionalized pyridine derivatives by an amidoalkylation/Staudinger/aza-Wittig sequence has been developed. The synthesis includes condensation of 3-azidopropanal with urea and p-toluenesulfinic acid followed by reaction of the N-[(3-azido-1-Tosyl)propyl]urea obtained with Na-enolates of Tosylacetophenone or acetyl acetone to give N-[(5-azido-1-oxo-1-phenyl-2-Tosyl)pent-3-yl]urea and 5-acetyl-6-(2-azidoethyl)-4-hydroxy-4-methylhexahydropyrimidin-2-one, respectively. These compounds are transformed into 6-phenyl-5-Tosyl-4-ureido- and 5-acetyl-6-methyl-4-ureido-1,2,3,4-tetrahydropyridines by treatment with PPh3. The former is aromatized under the action of MnO2 or reduced by NaBH4/CF3COOH system to provide 2-phenyl-3-Tosylpyridine and 2-phenyl-3-Tosyl-4-ureidopiperidine.

  • nucleophile mediated ring expansion of 4 chloromethyl and 4 mesyloxymethyl 5 Tosyl 1 2 3 4 tetrahydropyrimidin 2 ones to 6 Tosyl 2 3 4 5 tetrahydro 1h 1 3 diazepin 2 ones effect of the leaving group and the substituent at c6
    Tetrahedron, 2011
    Co-Authors: Anastasia A Fesenko, Anatoly D Shutalev
    Abstract:

    Abstract A five-step synthesis of 4-chloromethyl- and 4-mesyloxymethyl-5-Tosyl-1,2,3,4-tetrahydropyrimidin-2-ones has been developed. The reaction of N -[(2-benzoyloxy-1-Tosyl)ethyl]urea with sodium enolates of α-Tosylketones followed by cyclization–dehydration, and debenzoylation gave 4-hydroxymethyl-5-Tosyl-1,2,3,4-tetrahydropyrimidin-2-ones, which were transformed into the 4-chloromethyl- or 4-mesyloxymethyl-derivatives. Treatment of the latter with nucleophilic reagents, such as sodium cyanide, sodium diethyl malonate, sodium thiophenolate, or potassium phthalimide, afforded the corresponding 4,7-disubstituted 6-Tosyl-2,3,4,5-tetrahydro-1 H -1,3-diazepin-2-ones as a result of ring expansion. The effect of the leaving group and the substitution at the position C6 on the reactivity of the pyrimidines is discussed.