Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate
The reaction of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) with o-allylphenol gave 2-methylthiomethyl-2,3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N-tosylindoline in 85% yield.
Intramolecular Cyclisation Using Methyl(bismethylthio)sulphonium Salts. Part 3. Synthesis of 3,1-Benzoxazines.
The reaction of methyl(bismethylthio)sulphonium hexachloroantimonate (1) with 2-benzamido-, 2-acetamido-, and 2-phenylacetamido-1-isopropenylbenzene (2) - (4) leads to methylthio-functionalized 3,1-benzoxazine derivatives (8) - (10).The structures of the
Capozzi, Giuseppe,Ottana, Rosaria,Romeo, Giovanni,Valle, Giovanni
p. 1801 - 1833
(2007/10/02)
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