Access to Indoles via Diels–Alder Reactions of 5??Methylthio??2??vinylpyrroles with Maleimides

WE Noland, NP Lanzatella, RR Dickson…

Index: Noland, Wayland E.; Lanzatella, Nicholas P.; Dickson, Rozalin R.; Messner, Mary E.; Nguyen, Huy H. Journal of Heterocyclic Chemistry, 2013 , vol. 50, # 4 p. 795 - 808

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Abstract

Abstract Diels–Alder reactions of 5-methylthio-2-vinyl-1H-pyrroles with maleimides followed by isomerization gave tetrahydroindoles in moderate to good yield. Aromatization using activated MnO 2 in refluxing toluene gave the corresponding 2-methylthioindoles in good yields, and demethylthioation using Raney nickel gave the 2-H indoles in excellent yields. The protection of the adducts produced aromatization in improved yield, demonstrating ...