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Access to indoles via Diels‐Alder reactions of 3‐vinylpyrroles
Author(s) -
Noland Wayland E.,
Lanzatella Nicholas P.
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.228
Subject(s) - chemistry , saponification , isomerization , dehydrogenation , toluene , cycloaddition , methanol , organic chemistry , magnesium , medicinal chemistry , catalysis
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).