Intramolecular sulfoxide electrophilic sulfenylation in 1- and 3-acylindoles

Autor:	Dallas K. Bates, Qazi A. Habib
Rok vydání:	1995
Předmět:	chemistry.chemical_classification Reaction conditions chemistry.chemical_compound chemistry Sulfide Yield (chemistry) Intramolecular force Organic Chemistry Electrophile Sulfoxide Medicinal chemistry
Zdroj:	Journal of Heterocyclic Chemistry. 32:1477-1481
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570320511
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0f32e295bbbfac0808b6c0eb10f01e07 https://doi.org/10.1002/jhet.5570320511 Zobrazit plný text záznamu Plný text