Intramolecular sulfenylation using sulfoxides. preparation of 5H-pyrrolo[1,2-a][3,1]benzothiazines
Document Type
Article
Publication Date
8-1-1994
Abstract
N-[2-(Phenylsulfinylmethyl)phenyl]pyrrole (4) undergoes transfer sulfenylation to N-(2-chloromethylphenyl)-2-phenylthiopyrrole (5′) presumably via S-phenyl 5H-pyrrolo[1,2-a][3,1]benzothiazonium chloride (7). Depending upon the rigor of the reaction conditions, either N-(2-hydroxymethylphenyl)-2-phenylthiopyrrole (5) or its 5-trifluoroacetyl derivative (6) are obtained when 4 is treated with TFAA in trifluoroacetic acid. N-[2-(Methylsulfinylmethyl)aryl]pyrroles (12), when treated with gaseous hydrogen chloride and the resulting sulfonium salts refluxed in dichloroethane, produce substituted 5H-pyrrolo[1,2-a][3,1]benzothiazines (14). 1-Formyl-5H-pyrrolo[1,2-a][3,1]-benzothiazines (22) are formed in one step in good yield when sulfoxides (12) are reacted with the Vilsmeier-Haack reagent (DMF/POC13). No Pummerer rearrangement product is isolated from these reactions. © 1994.
Publication Title
Heterocycles
Recommended Citation
Picard, J.,
Chen, S.,
&
Bates, D.
(1994).
Intramolecular sulfenylation using sulfoxides. preparation of 5H-pyrrolo[1,2-a][3,1]benzothiazines.
Heterocycles,
38(8), 1775-1789.
http://doi.org/10.3987/com-93-6645
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/14171