A Conventional Route for the Synthesis of New Oxazolidin-2-one Derivatives with .BETA.-Aminoalanines

Abstract

A conventional new route to the novel oxazolidin-2-one derivatives (3a-f) having two substituents on N-3 and C-4 in the oxazolidin-2-one ring was established with racemic b b-aminoalanine derivatives (1) as the key starting materials.

Preferential Intramolecular Ring Closure of Aminoalcohols with Diethyl Carbonate to Oxazolidinones

“…The objective of this report is to explore the orientation of ring closure of aminoalcohol by (EtO) 2 CO. The compounds (1 7) and 6 8) ) are selected as the starting aminoalcohols, which have two hydroxy groups and a basic secondary amine in the molecules, so that the cyclization of these compounds employing (EtO) 2 CO can lead to the corresponding heterocycles (e.g.…”

“…

In connection with our interest in the chemistry of baminoalanines, [1][2][3][4] we have reported the synthetic application of these materials as a synthon for the preparation of a 5-membered oxazolidinone ring system.2) Some of the oxazolidinone derivatives have attracted much attention not only as a synthetic target but also because of the importance of the related compounds in the biological activities. 5,6) This paper deals with the relative rates of ring closure by cyclization with diethyl carbonate (EtO) 2 CO from aminoalcohols as starting material.

…”

“…In connection with our interest in the chemistry of baminoalanines, [1][2][3][4] we have reported the synthetic application of these materials as a synthon for the preparation of a 5-membered oxazolidinone ring system.…”

“…This paper deals with the relative rates of ring closure by cyclization with diethyl carbonate (EtO) 2 CO from aminoalcohols as starting material. We report here two typical experimental results for the cyclization that has two possibilities as a function of the ring intramolecular cyclization by (EtO) 2 CO.1…”

Antibacterial Activity of Some 5-Dialkylaminomethylhydantoins and Related Derivatives

“…[1][2][3][4][5] In our previous articles on chemical modifications of linezolid, we reported synthesis and antibacterial activity of new structural isomers of oxazolidin-2-ones as a general structure (A) 3) or a bioisosteric replacement 6) of the oxazolidinone ring in linezolid 7) by a hydantoin nucleus (B) (Fig. 1).…”