88460-88-2Relevant academic research and scientific papers
A FACILE SYNTHESIS OF dl-SEDAMINE AND dl-ALLOSEDAMINE
Ozawa, Naganori,Nakajima, Setsuko,Zaoya, Kyoko,Hamaguchi, Fumiko,Nagasaka, Tatsuo
, p. 889 - 894 (2007/10/02)
Racemic sedamine and dl-allosedamine were easily synthesized from the intermediate (3) using a cyclic acyliminium salt by the addition-elimination reaction sequence.
Base-catalyzed carbon-carbon bond formation reactions of ω-hydroxylactams
Speckamp, W. N.,Boer, J. J. J. de
, p. 410 - 414 (2007/10/02)
Active methylene compounds such as methyl ketones, 1,3-dicarbonyl systems and nitromethane condense under the influence of base with ω-hydroxylactams, thereby forming α-alkylated nitrogen heterocycles.The ease of alkylation is detemined by the position of a tautomeric equilibrium between ω-hydroxylactam and the open-chain amide-aldehyde, which is dependent upon the type of N-substituent and upon the lactam ring size.Some applications for the products obtained are indicated.
Carbon-carbon bond forming reactions of ω-oxylactams in acid and neutral medium
Speckamp, W. N.,Boer, J. J. J. de
, p. 405 - 409 (2007/10/02)
1,3-Dicarbonyl compounds and hydroxybenzenes condense under the influence of acid with ω-hydroxylactams 1-7 in an intermolecular process, thereby affording ω-alkylated lactams 8-13.The reactive intermediate in the carbon-carbon bond forming step is a cyclic N-acyliminium ion.The intramolecular variant affords keto ester 19.Upon activation of the ω-hydroxylactam as a hexafluoroisopropoxy ester, condensations with cyanide in aprotic polar solvents under neutral conditions become possible.
