An Efficient and Improved Route for the Preparation of (<i>S</i>)-5-Aminomethyloxazolidinone Libraries

Kim, Sang Woong; Lee, Jung‐Kyu; Lee, Eun Ju; Choo, Hea-Young Park; Yoo, Chung Youl; Lee, Dae Yon; Roh, Kyoung Rok; Kim, Eon Kyeom

doi:10.1021/cc0499237

Cited by 13 publications

(5 citation statements)

References 9 publications

(9 reference statements)

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“…3͑a͔͒ belongs to a class of substances with antibacterial and antimicrobial activities. [47][48][49] The first two electronic transitions are localized onto two different groups, and we show how they can be studied by selecting different model systems. Here we also consider the difference in the transition energies between the two excited states, ⌬E 1→2 = ⌬E 2 − ⌬E 1 .…”

Section: R-5-aminomethyl-2-oxazolidinonementioning

confidence: 99%

Using the ONIOM hybrid method to apply equation of motion CCSD to larger systems: Benchmarking and comparison with time-dependent density functional theory, configuration interaction singles, and time-dependent Hartree–Fock

Caricato

Vreven

Trucks

et al. 2009

The Journal of Chemical Physics

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Assessment of time-dependent density functional schemes for computing the oscillator strengths of benzene, phenol, aniline, and fluorobenzene J. Chem. Phys. 127, 084103 (2007) Equation of motion coupled-cluster singles and doubles ͑EOM-CCSD͒ is one of the most accurate computational methods for the description of one-electron vertical transitions. However, its O͑N 6 ͒ scaling, where N is the number of basis functions, often makes the study of molecules larger than 10-15 heavy atoms prohibitive. In this work we investigate how accurately less expensive methods can approximate the EOM-CCSD results. We focus on our own N-layer integrated molecular orbital molecular mechanics ͑ONIOM͒ hybrid scheme, where the system is partitioned into regions which are treated with different levels of theory. For our set of benchmark calculations, the comparison of conventional configuration interaction singles ͑CIS͒, time-dependent Hartree-Fock ͑TDHF͒, and time-dependent density functional theory ͑TDDFT͒ methods and ONIOM ͑with different low level methods͒ showed that the best accuracy-computational time combination is obtained with ONIOM͑EOM:TDDFT͒, which has a rms of the error with respect to the conventional EOM-CCSD of 0.06 eV, compared with 0.47 eV of the conventional TDDFT.

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Section: R-5-aminomethyl-2-oxazolidinonementioning

confidence: 99%

Using the ONIOM hybrid method to apply equation of motion CCSD to larger systems: Benchmarking and comparison with time-dependent density functional theory, configuration interaction singles, and time-dependent Hartree–Fock

Caricato

Vreven

Trucks

et al. 2009

The Journal of Chemical Physics

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“…In addition to the examples shown above, several other syntheses of chiral oxazolidinones have also been reported [44][45][46][47][48][49][50][51][52][53]. These include the aminohydroxylation of allylic carbamates [44], catalytic intramolecular aminopalladation [45], polymer supported synthesis and combinatorial synthesis of oxazolidinone libraries [46][47][48], and the conversion of racemic terminal epoxides under kinetic resolution condition [49].…”

Section: Synthesis Of the 5-hydroxyl Methyl Oxazolidinone Core Structurementioning

confidence: 94%

“…A general method for the preparation of cyclic carbamates is from 1,2 or 1,3-amino alcohol derivatives. Treating the amino alcohol with phosgene, triphosgene, carbonyl diimidazole (CDI) or other carbonylation reagents can allow the formation of cyclic carbamates [34][35][36][37][38][39][40][41][42][43][44][45][46].…”

Section: Synthesis Of the 5-hydroxyl Methyl Oxazolidinone Core Structurementioning

confidence: 99%

“…These include the aminohydroxylation of allylic carbamates [44], catalytic intramolecular aminopalladation [45], polymer supported synthesis and combinatorial synthesis of oxazolidinone libraries [46][47][48], and the conversion of racemic terminal epoxides under kinetic resolution condition [49].…”

Section: Synthesis Of the 5-hydroxyl Methyl Oxazolidinone Core Structurementioning

confidence: 99%

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Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Wang¹

2008

AIAMC

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Oxazolidinones are important synthetic antibacterial agents useful for the treatment of multi antibiotic resistant Gram-positive bacterial infections. Since the launch of Linezolid, the first member of the oxazolidinone antibacterial family, there have been many studies directed towards structural optimization and the development of second generation oxazolidinones. The N-aryl 5-acetamido methyl oxazolidinone is the core structure for this class of antibacterial agents and the oxazolidinone component is essential for antibacterial activities. The chiral cyclic carbamate 5-hydroxymethyloxazolidin-2-one and 6-hydroxymethyl-[1,3]oxazinan-2-one are also important building blocks for synthesizing other biologically active compounds. Because of the importance of these compounds, many methods have been developed for their facile syntheses. In the first part of this paper, the synthesis of Linezolid and its analogs, as well as the preparation of the oxazolidinone core structures, will be reviewed. Secondly, recent developments in the area of oxazolidinone antibacterial agents including structure-activity relationships will be reviewed.

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“…[20,21] Despite this significant activity, crosslinked POx networks beyond single-network hydrogels are rare with only a limited number of reports describing for example, double-network hydrogels, [22] organic-inorganic polymer hybrids, [23] and ternary organic-inorganic nanocomposite hydrogels. [24] To date, a small number of sequential POx IPNs have been described, [25][26][27] while there is only one report discussing the synthesis of simultaneous semi-IPNs. [28] The latter, however, were of a hydrophobic nature and only studied for their compatibility by differential scanning calorimetry.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous Interpenetrating Polymer Networks Based on Poly(2‐Oxazoline)s

Shah,

Trengove,

O'Connor

et al. 2023

Macro Materials & Eng

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Interpenetrating polymer networks (IPNs), comprised of two or more independent crosslinked networks in which the individual networks are interlaced, can be used to enhance material properties and increase functionality for applications such as tissue engineering, drug delivery, and biofabrication. IPNs can be formed by either simultaneous or sequential crosslinking, with sequential crosslinking being complicated by the need to infiltrate the constituents of the second network into the first network. Herein, the study reports the first simultaneous IPN based on the cationic ring‐opening polymerization (CROP) of 2‐methyl‐2‐oxazoline (MeOx) with bis(butyl‐2‐oxazoline) (BBOx) crosslinker and the reversible addition‐fragmentation chain‐transfer (RAFT) polymerization of N,N‐dimethylacrylamide (DMAAm) with N,N`‐methylene bis(acrylamide) (BAM) crosslinker. Specifically, the compatibility of the synthesis techniques is demonstrated for the preparation of simultaneous IPNs, and it is shown that, by varying the amounts of the two crosslinkers and comparing to single‐component networks, the equilibrium degree of swelling (EDS) in water and compressive modulus can be tuned. The results reported demonstrate the utility of CROP and RAFT for preparing IPNs and suggest that with appropriate optimization the technique can be expanded to other monomer pairs which are polymerizable via CROP and RAFT.

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An Efficient and Improved Route for the Preparation of (S)-5-Aminomethyloxazolidinone Libraries

Cited by 13 publications

References 9 publications

Using the ONIOM hybrid method to apply equation of motion CCSD to larger systems: Benchmarking and comparison with time-dependent density functional theory, configuration interaction singles, and time-dependent Hartree–Fock

Using the ONIOM hybrid method to apply equation of motion CCSD to larger systems: Benchmarking and comparison with time-dependent density functional theory, configuration interaction singles, and time-dependent Hartree–Fock

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Simultaneous Interpenetrating Polymer Networks Based on Poly(2‐Oxazoline)s

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