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Brönsted Acid-Catalyzed One-Pot Synthesis of Indoles from o-Aminobenzyl Alcohols and Furans

Alexey Kuznetsov, Anton Makarov, Aleksandr E. Rubtsov, Alexander V. Butin* and Vladimir Gevorgyan*

*University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, United States; Perm State University, 15 Bukireva Street, Perm 614990, Russian Federation, Email: vladuic.edu, alexander_butinmail.ru

A. Kutznetsov, A. Makarov, A. E. Rubtsov, A. V. Butin, V. Gevorgyan, J. Org. Chem., 2013, 78, 12144-12153.

DOI: 10.1021/jo402132p (free Supporting Information)


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Abstract

A Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans via in situ formation of aminobenzylfuran followed by its recyclization into the indole core proved to be efficient for a wide range of substrates. The resulting indoles can easily be transformed into other scaffolds, including 2,3- and 1,2-fused indoles, and indoles possessing an α,β-unsaturated ketone moiety at the C-2 position.


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Key Words

Indoles


ID: J42-Y2013