Synthesis and Antibacterial Activities of Chiral 1,3‐Oxazinan‐2‐one Derivatives.

Wang, Guijun; Ella‐Menye, Jean‐Rene; Sharma, Vibha

doi:10.1002/chin.200630176

Cited by 4 publications

(4 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although not utilized as extensively as 1,3-oxazolidin-2-ones, 1,3-oxazinan-2-ones are known to possess important biological activities, including antibacterial, 1 anticancer, 2 anti-HIV, 3 antidiabetic, 4 and anti-inflammatory properties (Figure 1 ). 5 They also serve as chiral auxiliaries 6 and intermediates in organic synthesis, including in the synthesis of natural products and pharmaceuticals.…”

Section: Table 1 Screening Of Reaction Conditions For T...mentioning

confidence: 99%

Trifluoroethanol-Mediated Cyclization of Two-Carbon-Tethered Epoxide–N-Boc Pairs: Completely Regioselective Synthesis of 3,6-Disubstituted 1,3-Oxazinan-2-ones

Das¹,

Chouhan²,

Borgohain³

et al. 2023

Synthesis

View full text Add to dashboard Cite

The regio- and diastereoselective construction of biologically relevant cyclic carbamates under operationally simple and mild transition metal-free is challenging and has led to a demand for efficient methods for their synthesis. The intramolecular ring-opening cyclization of N-Boc-tethered epoxides leading to the formation of cyclic carbamates is equipped with many favorable synthetic features, including easy accessibility of starting materials in a stereodefined form, high diversification points in the substrates, and favorable entropy factor. However, its use in the construction of 1,3-oxazinan-2-ones remains largely neglected. Specifically, prior to 2020, only few 1,3-oxazinan-2-ones were successfully synthesized using this strategy. Moreover, our very own recent attempt to access these heterocycles using one-carbon-tethered N-Boc/epoxide pairs was met with a little success as the process furnished either only 1,3-oxazolidin-2-ones or nearly equal amounts of 1,3-oxazolidin-2-ones and 1,3-oxazinan-2-ones. Herein, we demonstrate that when the epoxide and N-Boc moieties are connected by a two-carbon tether, the cyclization could deliver 1,3-oxazinan-2-ones containing vicinal stereocenters, as sole regio- and diastereomers in high yields (up to 95% yield), irrespective of whether the distal epoxide substituent is alkyl or aryl, or the epoxide is cis- or trans-configured.

show abstract

Section: Table 1 Screening Of Reaction Conditions For T...mentioning

confidence: 99%

Trifluoroethanol-Mediated Cyclization of Two-Carbon-Tethered Epoxide–N-Boc Pairs: Completely Regioselective Synthesis of 3,6-Disubstituted 1,3-Oxazinan-2-ones

Das¹,

Chouhan²,

Borgohain³

et al. 2023

Synthesis

View full text Add to dashboard Cite

show abstract

“…Infections caused by methicillin resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) can be life threatening especially for immunocompromised patients due to HIV, surgery or any other illness [1,2]. The human immunodeficiency virus (HIV) pandemic has increased the incidence of tuberculosis (TB) too [3].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial, antifungal and antimycobacterial activities of some pyrazoline, hydrazone and chalcone derivatives

Evranos-Aksöz

Onurdağ

Özgacar

2015

Zeitschrift Für Naturforschung C

View full text Add to dashboard Cite

Twenty-seven previously reported chalcones and their pyrazoline and hydrazone derivatives as well as two further chalcones have been screened for their antimicrobial, antifungal and antimycobacterial activities against standard microbial strains and drug resistant isolates. The minimum inhibitory concentration (MIC) value of each compound was determined by a two-fold serial microdilution technique. The compounds were found to possess a broad spectrum of antimicrobial activities with MIC values of 8-128 μg/mL. One compound [(E)-1-(4-hydroxyphenyl)-3-p-tolylprop-2-en-1-one] had equal activity with gentamycin (8 μg/mL) against Enterococcus faecalis. Chalcones were found to be more active than their hydrazone and 2-pyrazoline derivatives against Staphylococcus aureus ATCC 29213 and E. faecalis ATCC 29212.

show abstract

“…Oxazinan-2-ones (Figure ) are compounds of interest due to their biological activity as they have been employed in the treatment for Alzheimer’s disease, in herbicides with excellent crop–weed selectivity, in the treatment of diseases mediated by the activation of β3-adrenoceptor, in the treatment of diseases related to kinases activity, and for the regulation of cholesterol . There are many routes to oxazinan-2-ones, and the majority involve phosgene and isocyanate , (synthesis D, Scheme ) or alkyl halide − chemistry (synthesis C, Scheme ), while others require hard to obtain starting materials − or multiple steps to give the final product. , Recently, we have reported two new routes to 1,3-oxazinan-2-ones (syntheses A and B, Scheme ) by a one-pot reaction of an amine with a 1,3-diol and a dialkyl carbonate (DAC) in the presence of a strong base. , …”

Section: Introductionmentioning

confidence: 99%

A Comparative Environmental Assessment for the Synthesis of 1,3-Oxazin-2-one by Metrics: Greenness Evaluation and Blind Spots

Toniolo

Aricò

Tundo

2014

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Alternative syntheses for the production of 3-benzyl-1,3-oxazinan-2-one are compared and evaluated employing green metrics. An environmental assessment has been performed using the algorithm recently developed by Andraos that takes into account the mass flows and the software EATOS that considers mass flows, environmental impacts of the substances involved, and waste produced. Strengths and critical spots of the environmental tools employed are also discussed. Data collected showed that the synthesis employing diethyl carbonate is the most promising one, having the lowest environmental impact.

show abstract

Synthesis and Antibacterial Activities of Chiral 1,3‐Oxazinan‐2‐one Derivatives.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 4 publications

References 1 publication

Trifluoroethanol-Mediated Cyclization of Two-Carbon-Tethered Epoxide–N-Boc Pairs: Completely Regioselective Synthesis of 3,6-Disubstituted 1,3-Oxazinan-2-ones

Trifluoroethanol-Mediated Cyclization of Two-Carbon-Tethered Epoxide–N-Boc Pairs: Completely Regioselective Synthesis of 3,6-Disubstituted 1,3-Oxazinan-2-ones

Antibacterial, antifungal and antimycobacterial activities of some pyrazoline, hydrazone and chalcone derivatives

A Comparative Environmental Assessment for the Synthesis of 1,3-Oxazin-2-one by Metrics: Greenness Evaluation and Blind Spots

Contact Info

Product

Resources

About