- 1-Acyldeoxyvasicinone salts as effective intermediate C- and N-acylating agents for alkaloids and amino acids
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The reaction of deoxyvasicinone with acid chlorides of aliphatic (acetylbromide) and aromatic (benzoyl-, o-, p-methoxy-, p-nitrobenzoylchlorides) acids was studied. It was shown that 1-deoxyvasicinone salts were formed at room temperature; α-aroyloxymethylidenedeoxyvasicinones, in the presence of triethylamine at 80-85°C. It was found that acid chlorides cause 1-acyldeoxyvasicinone salts to transform into α-hydroxy-or α-aroyloxyarylidenedeoxyvasicinones, which indirectly confirmed their acylating properties. It was found that 1-acyldeoxyvasicinone salts were effective acylating agents for alkaloids (cytisine, 1,2-dihydrodeoxyvasicinone) and amino acids (glycine, β-alanine, α-aminobutyric acid) and can be used to acylate primary and secondary aliphatic and heterocyclic amines.
- Shakhidoyatov,Genjemuratova,Oripov
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p. 718 - 723
(2008/02/08)
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- New reactions of Deoxyvasicinone. Part 3.
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The reaction of deoxyvasicinone 1 with benzoic anhydride, bis(dimethylamino)methane and amyl nitrite are reported.Metallation of 1 is also described.
- Dunn, A. D.,Kinnear, K. I.
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p. 311 - 312
(2007/10/02)
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