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1 article(s) from Lippa, Rhys A

Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner–Wadsworth–Emmons-based approach

Rhys A. Lippa,
John A. Murphy and
Tim N. Barrett

Beilstein J. Org. Chem. 2020, 16, 1617–1626, doi:10.3762/bjoc.16.134

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Graphical Abstract

Figure 1: The Arg–Gly–Asp tripeptide sequence and examples of tetrahydro-1,8-naphthyridine-containing integri...

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Scheme 1: Commonly used synthetic routes to tetrahydro-1,8-naphthyridine moieties by hydrogenation of saturat...

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Scheme 2: Previous synthetic route to fluoropyrrolidine 6 utilising a Wittig reaction and the novel, higher y...

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Scheme 3: Synthesis of phosphoramidate 9 from tetrahydro-1,8-naphthyridine 8. Conditions: s-BuLi (3 equiv), d...

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Scheme 4: Mono- and diphosphorylation of tetrahydro-1,8-naphthyridine 11. Conditions: (i) s-BuLi (2 equiv), d...

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Scheme 5: Synthesis of amine 6 from phosphonate 7 and aldehyde 5. Conditions: (i) T3P^® (50% w/w in DCM, 3 equ...

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Scheme 6: Monodeuteration of 13 as observed by ¹H and ¹³C NMR. Conditions: s-BuLi (3 equiv), THF, −42 °C, 20 ...

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Scheme 7: Sequential diphosphorylation of tetrahydronaphthyridine 11. Conditions: (i) iPrMgCl (1.5 equiv), TH...

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Scheme 8: Possible mechanistic pathways for the formation of dimer 28. Conditions: KOt-Bu, THF, 1 h, 68% yiel...

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Scheme 9: Alkylation of phosphoramidate 13 by iodide 29 to afford compound 30 and byproducts alcohol 31 and d...

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Published 08 Jul 2020

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