Carbonation of natural α-amino acids in water and subsequent cyclization with (2-bromo-1-arylethyl)dimethylsulfonium bromides led selectively to a family of 2-oxazolidinonyl derivatives, which were isolated without the needing of purification. Analogous conjugation of the 2-oxazolidinone skeleton with amino acids was previously realized by complicated and narrow-scope routes, whereby the amino acid core is built stepwise. Deprotonation of some of the products afforded the corresponding water-soluble carboxylates, while a straightforward, proof of concept esterification reaction of the carboxylic acid group yielded a menthol-alanine-oxazolidinone conjugate.

Trapping carbamates of α-Amino acids: One-Pot and catalyst-free synthesis of 5-Aryl-2-Oxazolidinonyl derivatives

Bresciani G.;Zacchini S.;Pampaloni G.;Marchetti F.
2021

Abstract

Carbonation of natural α-amino acids in water and subsequent cyclization with (2-bromo-1-arylethyl)dimethylsulfonium bromides led selectively to a family of 2-oxazolidinonyl derivatives, which were isolated without the needing of purification. Analogous conjugation of the 2-oxazolidinone skeleton with amino acids was previously realized by complicated and narrow-scope routes, whereby the amino acid core is built stepwise. Deprotonation of some of the products afforded the corresponding water-soluble carboxylates, while a straightforward, proof of concept esterification reaction of the carboxylic acid group yielded a menthol-alanine-oxazolidinone conjugate.
Bresciani, G.; Zacchini, S.; Famlonga, L.; Pampaloni, G.; Marchetti, F.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/1105548
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 2
  • ???jsp.display-item.citation.isi??? 1
social impact