Synlett

Anionic ortho-Fries Rearrangement, a Facile Route to Arenol-Based Mannich Bases

N Assimomytis, Y Sariyannis, G Stavropoulos…

Index: Assimomytis, Nikos; Sariyannis, Yiannis; Stavropoulos, Georgios; Tsoungas, Petros G.; Varvounis, George; Cordopatis, Paul Synlett, 2009 , # 17 p. 2777 - 2782

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Citation Number: 10

Abstract

Abstract Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol- based carbamates makes the rearrangement an exclusive reaction, even at-90 C, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino) methyl]-8-hydroxy-1-naphthaldehydes is ...

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