Synthesis of potentially bioactive PABA-related N-(aminoalkyl)lactamic amino acids and esters via selective S sub(N)Ar reactions

Synthesis of potentially bioactive PABA-related N-(aminoalkyl)lactamic amino acids and esters via selective S sub(N)Ar reactions

Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by S sub(N)Ar reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition-elimination S sub(N)Ar mechanism was confi...

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Veröffentlicht in:Amino acids 2011-01, Vol.40 (1), p.197-204
Hauptverfasser: Goncalves, Renato S, Abdelnur, Patricia V, Santos, Vanessa G, Simas, Rosineide C, Eberlin, Marcos N, Magalhaes, Alvicler, Perez Gonzalez, Eduardo R
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols
Amino acids
Esterification
Esters
Nuclear magnetic resonance
Synthesis
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Zusammenfassung:Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by S sub(N)Ar reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition-elimination S sub(N)Ar mechanism was confirmed by NMR and MS measurements. Graphical Abstract:
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-010-0634-z