Intramolecular capture of pummerer rearrangement intermediates. I. Synthesis of pyrrolo[2,1‐c][1,4]benzothiazines
Document Type
Article
Publication Date
1-1-1986
Department
Department of Chemistry; Department of Chemical Engineering
Abstract
Treatment of 1‐(2‐alkylsulfinylphenyl)pyrroles with trifluoroacetic acid in refluxing toluene gives 4‐substituted pyrrolo[2,1‐c][1,4]benzothiazines in good yield when the alkyl group bears an electron withdrawing substituent on the α‐carbon. In the absence of such a group, starting material is recovered. The sulfoxides are prepared by oxidation (mCBPA) of the corresponding sulfide. The sulfides are prepared from 2‐aminobenzenethiol either by S‐alkylation followed by conversion to the pyrrole using 1,4‐dimethoxytetrahydrofuran in glacial acetic acid or by S‐alkylation of 1‐(2‐phenylmercapto)pyrrole followed by oxidation to the sulfoxide.
Publication Title
Journal of Heterocyclic Chemistry
Recommended Citation
Bates, D.,
Winters, R.,
&
Sell, B.
(1986).
Intramolecular capture of pummerer rearrangement intermediates. I. Synthesis of pyrrolo[2,1‐c][1,4]benzothiazines.
Journal of Heterocyclic Chemistry,
23(3), 695-699.
http://doi.org/10.1002/jhet.5570230311
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/3746
Publisher's Statement
Copyright © 1986 Journal of Heterocyclic Chemistry. Publisher’s version of record: https://doi.org/10.1002/jhet.5570230311