Diethoxymethyl Protected Indoles: Synthesis and Regioselective Transformations

Gmeiner P (1996)

Publication Type: Journal article

Publication year: 1996

Journal

Synthesis-Stuttgart Thieme Publishing / Georg Thieme Verlag

Publisher: Thieme Publishing / Georg Thieme Verlag

Pages Range: 1196-1198

Abstract

Reaction of the indoles 1a-d with triethyl orthoformate gives access to the N-diethoxymethyl derivatives 2a-d. Convenient and mild removal of the diethoxymethyl substituent is possible by subsequent treatment of 2a-d with aqueous HCl and NaOH. Using 2a as an example, it could be shown that deprotonation followed by addition of an electrophile (Me3SiCl or Bu3SnCl) leads to substitution in position 2. Further functionalization was possible by palladium-catalyzed coupling reactions starting from the stannane 4. The diethoxymethyl protected η⁶-tricarbonylchromium complex 5 facilitated acylation in position 2 after deprotonation.

Authors with CRIS profile

Peter Gmeiner Lehrstuhl für Pharmazeutische Chemie

How to cite

APA:

Gmeiner, P. (1996). Diethoxymethyl Protected Indoles: Synthesis and Regioselective Transformations. Synthesis-Stuttgart, 1196-1198.

MLA:

Gmeiner, Peter. "Diethoxymethyl Protected Indoles: Synthesis and Regioselective Transformations." Synthesis-Stuttgart (1996): 1196-1198.

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