Journal
SYNLETT
Volume -, Issue 17, Pages 2777-2782Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1217991
Keywords
rearrangements; reductions; Mannich bases; carbamates; ortho-Fries rearrangement
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Funding
- European Social Fund (ESF)
- Operational Programme for Educational Training (EPEAEK)
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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 degrees 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 presented.
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