Advances toward the Synthesis of Functionalized γ-Lactams

Rivas, Fátima; Ling, Taotao

doi:10.1080/00304948.2016.1165059

Cited by 56 publications

(23 citation statements)

References 67 publications

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“…γ‐Lactams are important organic heterocycles that are found in nature and often exhibit interesting biological activities They are easily available and are applied in industry for large‐scale ring‐opening polymerizations . Especially, γ‐spirolactams of the general structure 1 (Figure ) have attracted much attention as potential medicinal agents and can be synthesized by various methods, but over many steps .…”

Section: Introductionmentioning

confidence: 99%

Simple Synthesis of γ‐Spirolactams by Birch Reduction of Benzoic Acids

et al. 2017

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A convenient synthesis of γ‐spirolactams in only two steps was developed. Birch reduction of benzoic acids and immediate alkylation with chloroacetonitrile afforded cyclohexadienes in high yields. The products could be isolated by crystallization on a large scale in analytically pure form. Subsequent hydrogenation with platinum(IV) oxide as the catalyst reduced the nitrile functionality and the double bonds in the same step with excellent stereoselectivity. The relative configurations were determined unequivocally by X‐ray analyses. Direct cyclization of the intermediary formed amino acids afforded the desired γ‐spirolactams in excellent overall yields. The procedure is characterized by few steps, cheap reagents, and can be performed on a large scale, interesting for industrial processes.

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Section: Introductionmentioning

confidence: 99%

Simple Synthesis of γ‐Spirolactams by Birch Reduction of Benzoic Acids

et al. 2017

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“…4 This biological activity has made the synthesis of polycyclic γ-lactams quite attractive, and several straightforward and robust methods for the construction of polycyclic γ-lactams have been elegantly established. 5 …”

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confidence: 99%

Construction of Polycyclic γ-Lactams and Related Heterocycles via Electron Catalysis

2016

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Cascade radical cyclization of 1,6-enynes for the construction of biologically important polycyclic γ-lactams and related heterocycles is reported. In these radical cascade processes, three new C–C bonds are formed and transition metals are not required to run these sequences. The mild reaction conditions, broad substrate scope, and the importance of the heterocyclic products render the approach valuable.

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“…The βlactams are one of the best known and intensively investigated ring systems due to both their utility as synthetic intermediates and their biological activity as antibiotics [31][32][33]. In the same vein, γ-lactams are at the heart of a number of medicinally and biologically important compounds, as well as a large collection of natural products, and the synthesis of functionalised γ-lactams is therefore attracting increased attention [34,35]. Very recently, a palladium-catalysed route to functionalised γ-lactams Scheme 1: Plausible formation mechanism for the lactams formed by carbonylation of in situ-generated iPr 2 N-C-TMP.…”

Section: Resultsmentioning

confidence: 99%