New Simple Synthesis of N-Substituted 1,3-Oxazinan-2-ones

Trifunović, Srećko R.; Dimitrijevic, D; Vasić, Gordana; Radulović, Niko S.; Vukićević, Mirjana; Heinemann, Frank W.; Vukićević, Rastko D.

doi:10.1055/s-0029-1218642

Cited by 8 publications

(1 citation statement)

References 20 publications

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“…Most of the synthetic routes to 1,3-oxazinan-2-ones involves phosgene or its derivatives (Murdock, 1968), alkyl halide chemistry (Trifunovic et al, 2010) and isocyanate compounds (Shibata et al, 1989). In the literature, there are also other procedures that generally require complex starting materials or multiple-step pathways, in order to achieve the final product (Mangelinckx et al, 2010).…”

Section: -Membered Heterocyclesmentioning

confidence: 99%

Dialkyl Carbonates in the Green Synthesis of Heterocycles

2019

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This review focuses on the use of dialkyl carbonates (DACs) as green reagents and solvents for the synthesis of several 5- and 6-membered heterocycles including: tetrahydrofuran and furan systems, pyrrolidines, indolines, isoindolines, 1,4-dioxanes, piperidines, and cyclic carbamates. Depending on the heterocycle investigated, the synthetic approach used was different. Tetrahydrofuran systems, pyrrolidines, indolines, isoindoline, and 1,4-dioxanes were synthesized using dimethyl carbonate (DMC) as sacrificial molecule (B Ac 2/B Al 2 mechanism). Cyclic carbamates, namely 1,3-oxazin-2-ones, were prepared employing DACs as carbonylating agents, either by B Ac 2/B Al 2 mechanism or through a double B Ac 2 mechanism. Piperidines were synthetized taking advantage of the anchimeric effect of a new family of dialkyl carbonates, i.e., mustard carbonates. Finally, in the case 5-hydroxymethylfurfural (HMF), DMC has been employed as efficient extracting solvent of this extensively investigated bio-based platform chemical from the reaction mixture. These synthetic approaches demonstrate, once again, the great versatility of DACs and their—yet to be fully explored—potential as green reagents and solvents in the synthesis of heterocycles.

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