Synthesis and transformation of 6-aminomethyl derivatives of 7-hydroxy-2'-fluoroisoflavones
Keyword(s):
Mannich aminomethylation of 8-methyl-7-hydroxy-2'-fluoroisoflavones applying bis-(N,N-dimethylamino)methane afforded C-6 substituted N,N-dimethylaminomethyl derivatives. Subsequent acetylation of these compounds in acetic anhydride in the presence of potassium acetate provided access to the corresponding acetoxymethyl derivatives that were converted to hydroxymethyl- and alkoxymethyl-substituted 7-hydroxyisoflavonoids. Addition of 3-(N,N-dimethylamino)-5,5-dimethyl-2-cyclohexen-1-one or 1,3-dimethyl-5-aminopyrazole with thermally generated ortho-quinone methides led to hetero-Diels–Alder or Michael adducts.
Inverse electron demand Diels–Alder reactions with aminomethyl derivatives of 3-arylhydroxycoumarins
2016 ◽
Vol 52
(7)
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pp. 460-466
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2016 ◽
Vol 71
(3)
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pp. 267-271
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2012 ◽
Vol 9
(6)
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pp. 633-637
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2002 ◽
Vol 57
(6)
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pp. 637-644
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