24845-02-1Relevant academic research and scientific papers
Polycondensed heterocycles. IX. Pyrrolo[2,1-c][1,4]benzothiazepines. Synthesis of 3-(dimethylamino)methyl derivatives
Garofalo, Antonio,Campiani, Giuseppe,Ciani, Silvia M.,Fiorini, Isabella,Nacci, Vito
, p. 7745 - 7754 (2007/10/03)
The synthesis of 3-(dimethylamino)methyl-5H,11H-pyrrolo[2,1- c][1,4]benzothiazepine derivatives 2a-c which might show significant central nervous system (CNS) activity, is described. The basic side chain was introduced by a Mannich condensation with the p
Neighbouring Group Effects in a Pummerer-Type Rearrangement: A Facile Entry into 3,1-Benzoxathiins
Kersey, Ian D.,Fishwick, Colin W. G.,Findlay, John B. C.,Ward, Peter
, p. 6819 - 6834 (2007/10/02)
Arylmethyl sulphoxides treated with trialkylsilyl halide and base undergo a Pummerer-type rearrangement to give α-siloxy and α-chlorosulphides.However, the presence of an ortho hydroxymethyl group results in the exclusive and efficient formation of the α-chlorosulphides, presumably mediated via an intramolecular attack to yield an alkoxysulphonium salt.These 2-(hydroxymethyl)aryl chloromethylsulphides can then be converted into the corresponding 3,1-benzoxathiins via an intramolecular cyclisation.Preliminary investigation of the chemistry of these 3,1-benzoxathiins, reveals that in one case, a novel base induced ring contraction occurs to yield a benzothiophene.
