One-pot, multicomponent, diastereoselective, green synthesis of 3,4-dihydro-2H-benzo[b][1,4]oxazine analogues.

doi:10.1021/acs.joc.0c00463

Paper

One-pot, multicomponent, diastereoselective, green synthesis of 3,4-dihydro-2H-benzo[b][1,4]oxazine analogues.

Published May 14, 2020 · N. Kushwaha, B. Kushwaha, R. Karpoormath

The Journal of organic chemistry

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Abstract

A novel green and efficient catalyst-free, the mild one-pot, multicomponent synthetic strategy has been developed to construct substituted 3,4-dihydro-2H-benzo[b][1,4]oxazine. This reaction proceeds via in-situ formation of Schiff-base followed by base mediated alkylation with phenacyl bromide/substituted phenacyl bromide, finally leading to intramolecular cyclization to give a mixture of diastereomers with excellent diastereoselectivity (up to dr = 99:1), which were isolated as single diastereomer in moderate to excellent yields (41-92%). Besides, this new versatile methodology provides a wide scope for the synthesis of differ-ent functionally substituted benzoxazine scaffolds and can be further exploited as building blocks for the synthesis of multifacet-ed molecular structures, especially for pharmaceutical applications.

Study Snapshot

This green, efficient one-pot strategy efficiently synthesizes substituted 3,4-dihydro-2H-benzo[b][1,4]oxazine analogues with excellent diastereoselectivity, offering potential for pharmaceutical applications.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

One-pot, multicomponent, diastereoselective, green synthesis of 3,4-dihydro-2H-benzo[b][1,4]oxazine analogues.

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References

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This efficient and simple method efficiently synthesizes nonracemic 1,4-benzoxazines with excellent enantio- and diastereospecificity, offering a short and efficient synthesis to (S)-3-methyl-1,4-benzoxazine (S)-3v, a

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Citations

Sustainable synthesis of antibacterial 3-aryl-2H-benzo[b,1,4]oxazin-2-ones via SNAr Csp2–Csp2 coupling

Microwave-assisted SNAr synthesis efficiently synthesizes promising antibacterial compounds, with potential for further biological evaluation to combat antibiotic resistance.

A transition-metal-free multicomponent reaction towards constructing chiral 2H-1,4-benzoxazine scaffolds

This transition-metal-free multicomponent reaction efficiently constructs chiral 2H-1,4-benzoxazine derivatives with excellent functional-group tolerance, offering a novel approach for biologically important benzoxazine scaffolds.