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Access to indoles via Diels-Alder reactions of 3-vinylpyrroles

✍ Scribed by Wayland E. Noland; Nicholas P. Lanzatella

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
178 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image
N‐p‐Toluenesulfonyl‐3‐vinylpyrrole underwent endo‐addition [4 + 2] cycloaddition reactions with maleimides and benzoquinones, followed by isomerization to give tetrahydroindoles in good yields. Dehydrogenation with activated MnO~2~ in refluxing toluene gave the corresponding indoles in fair to good yields. Detosylation via saponification or with magnesium in refluxing methanol gave the N‐H indoles in moderate to good yields. This method for formation of indoles is both convergent and versatile and uses starting materials that are conveniently prepared. J. Heterocyclic Chem., (2009).

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