Novel domino reactions for the efficient synthesis of 5,6-dihydro-1,4,2-oxathiazines

[Display omitted] A facile efficient synthesis of novel 3-aryl-5,6-dihydro-1,4,2-oxathiazin-6-ols from the reaction of (E)-N-hydroxyarylimidoyl chlorides and 1,4-dithiane-2,5-diol in the presence of triethylamine is described. This transformation presumably proceeds via in situ generation of 2-merca...

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Bibliographic Details
Published in:Tetrahedron letters 2014-07, Vol.55 (28), p.3761-3764
Main Authors: Vivek Kumar, Sundaravel, Perumal, Subbu
Format: Article
Language:English
Subjects:
(E)-N-Hydroxyarylimidoyl chloride
1,4-Dithiane-2,5-diol
3-Aryl-5,6-dihydro-1,4,2-oxathiazin-6-ol
Chemical reactions
Chlorides
Domino reactions
Nitriles
Organic chemistry
Oxides
Synthesis
Tetrahedrons
Transformations
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Summary:[Display omitted] A facile efficient synthesis of novel 3-aryl-5,6-dihydro-1,4,2-oxathiazin-6-ols from the reaction of (E)-N-hydroxyarylimidoyl chlorides and 1,4-dithiane-2,5-diol in the presence of triethylamine is described. This transformation presumably proceeds via in situ generation of 2-mercaptoacetaldehyde and nitrile oxide and their concomitant [3+3] annulation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.05.062