107835-88-1Relevant articles and documents
Convenient synthesis of oxazolidinones by the use of halomethyloxirane, primary amine, and carbonate salt
Osa, Yumiko,Hikima, Yuka,Sato, Yoko,Takino, Kouichi,Ida, Yoshihiro,Hirono, Shuichi,Nagase, Hiroshi
, p. 5737 - 5740 (2005)
Primary amines reacted with carbonate salts (Na2CO3, K2CO3, Cs2CO3, and Ag 2CO3) and halomethyloxiranes in the presence of a base such as DBU or TEA to give oxazolidinones in high yields. The use of K 2CO3 among these carbonate gave the best yield in this synthesis. A reaction mechanism was proposed that the oxazolidinone was obtained from an oxazinanone intermediate via a bicyclo[2.2.1] intermediate. The present reaction can be widely applied to convenient synthesis of useful N-substituted oxazolidinones and chiral oxazolidinones.
Discovery of oxazolidinone-based heterocycles as subtype selective sigma-2 ligands
Blass, Benjamin E.,Bhandare, Richie Rashmin,Canney, Daniel J.
, p. 416 - 425 (2022/01/31)
The sigma-2 (σ2) receptor, also known as the Transmembrane Protein 97 (TMEM97, and MAC30 (Meningioma-associated protein), has been linked to a number of conditions are disease states such as schizophrenia, cancer, Alzheimer’s disease, traumatic brain injury, and neuropathic pain. As part or our on-going effort identify novel σ2 ligands, we have identified a series of novel, functionalized oxazolidin-2-one sigma-2 ligands (4). Our lead compound (4h) demonstrated high affinity (Ki = 36 nM) and excellent σ1/σ2 selectivity (79-fold). Evaluation of its affinity at key CNS targets via the Psychoactive Drug Screening Program (PDSP) also indicated a high degree of selectivity for σ2 over other receptors. [Figure not available: see fulltext.].
Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products
Rintjema, Jeroen,Epping, Roel,Fiorani, Giulia,Martín, Eddy,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
, p. 3972 - 3976 (2016/03/19)
Substituted epoxy alcohols and amines allow substrate-controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2-derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile-assisted ring-opening step following an SNi pathway, and a 5-exo-tet cyclization, thus leading to heterocyclic scaffolds.
