Intramolecular sulfoxide electrophilic sulfenylation in 2- and 3-indoleanilides
Document Type
Article
Publication Date
12-3-2007
Abstract
When N-[2-(alkylsulfinyl)phenyl]-1H-indole-2-carboxamides with varying degrees of indolic and amidic N-alkylation are heated in an inert solvent or treated with trifluoroacetic anhydride; only compounds in which the amidic nitrogen is methylated cyclize to indolo[3,2-b]-1,5-benzothiazepinones (9, 10). Successful cyclization is attributed to the ability of N-Me amides to readily adopt a conformation conducive to cyclization, which other derivatives are unable to achieve. The analogous 3-indoleanilide, N,N-dimethyl N-[2-(ethylsulfinyl)phenyl]-1H-indole-3-carboxamide (17a), undergoes SES/rearrangement to produce 10 upon heating in p-xylene. An intermediate 3H-indolinium spirocyclic species is proposed to account for this result. © 2007 Elsevier Ltd. All rights reserved.
Publication Title
Tetrahedron
Recommended Citation
Eggers, M.,
Jog, P.,
&
Bates, D.
(2007).
Intramolecular sulfoxide electrophilic sulfenylation in 2- and 3-indoleanilides.
Tetrahedron,
63(49), 12185-12194.
http://doi.org/10.1016/j.tet.2007.09.050
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/7149