Anionic ortho-Fries Rearrangement, a Facile Route to Arenol-Based Mannich Bases
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Assimomytis, N.
Sariyannis, Y.
Stavropoulos, G.
Tsoungas, P. G.
Varvounis, G.
Cordopatis, P.
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Thieme Publishing
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peer reviewed
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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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rearrangements, reductions, mannich bases, carbamates, ortho-fries rearrangement, directed ortho-metalation, regiospecific route, organic-synthesis, secondary-amines, ortho-lithiation, tertiary amides, one-pot, reduction, phenols, derivatives
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<Go to ISI>://000271904100009
https://www.thieme-connect.de/ejournals/pdf/10.1055/s-0029-1217991.pdf
https://www.thieme-connect.de/ejournals/pdf/10.1055/s-0029-1217991.pdf
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en
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Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας