Intramolecular sulfoxide electrophilic sulfenylation in 1‐ and 3‐acylindoles
Document Type
Article
Publication Date
1-1-1995
Department
Department of Chemistry
Abstract
Heating 1‐(2‐ethylsulfinyl)benzoylindole 1 in refluxing p‐xylene [thermal Sulfoxide Electrophilic Sulfenylation (SES)] produces indolo[2,1‐b][1,3]benzothiazin‐12‐one 2 in 66% yield. Similar treatment of 1‐methyl‐3‐(2‐ethylsulfinyl)benzoylindole 8 provides three products: sulfide 7 and cyclized products 9 and 10 in 10, 19 and 15% yield, respectively. Conversion of 10 to 9 under the reaction conditions is demonstrated and a spirocyclic intermediate 12, which may form from both 9 and 10 but undergoes only preferential S‐migration, is postulated to account for the rearrangement.
Publication Title
Journal of Heterocyclic Chemistry
Recommended Citation
Bates, D.,
&
Habib, Q.
(1995).
Intramolecular sulfoxide electrophilic sulfenylation in 1‐ and 3‐acylindoles.
Journal of Heterocyclic Chemistry,
32(5), 1477-1481.
http://doi.org/10.1002/jhet.5570320511
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/3747
Publisher's Statement
Copyright © 1995 Journal of Heterocyclic Chemistry. Publisher’s version of record: https://doi.org/10.1002/jhet.5570320511