Synthesis of [1,2,4]Triazolo[4,3- a]piperazin-6-ones: An Approach to the Triazole-Fused Ketopiperazine Scaffold

Organic Letters
Khoubaib Ben Haj SalahSéverine Denoyelle

Abstract

A stereoconservative synthesis to access the triazole-fused ketopiperazine (TKP) scaffold is presented. This underexplored platform offers a wide range of structural modulations with several points of diversity and chiral centers. A series of [1,2,4]triazolo[4,3- a]piperazin-6-ones was synthesized from optically pure dipeptides. The methodology was then successfully applied to access the pyrrolo[1,2- a]triazolo[3,4- c]piperazin-6-one tricycle. Importantly, the crystal structures of representative TKPs confirmed that the configuration of the chiral centers was controlled during the synthetic route and facilitated description of the orientation of the substituents depending on their nature and position on the TKP scaffold.

References

May 11, 2002·The Journal of Organic Chemistry·Yukio HitotsuyanagiKoichi Takeya
Nov 11, 2011·Mini Reviews in Medicinal Chemistry·C CornacchiaF Pinnen
May 2, 2012·Chemical Society Reviews·Corien de GraaffRomano V A Orru
Oct 15, 2013·Applied Biochemistry and Biotechnology·S Nishanth Kumar, Bala Nambisan
Dec 2, 2014·Bioorganic & Medicinal Chemistry Letters·Anne-Laure BlayoJean-Alain Fehrentz
Feb 15, 2015·European Journal of Medicinal Chemistry·Xueqing ChenWenhan Lin
Feb 16, 2016·Beilstein Journal of Organic Chemistry·Samantha CaputoLuca Banfi
Jan 1, 2015·European Journal of Organic Chemistry·Tryfon Zarganes-TzitzikasAlexander Dömling
Apr 14, 2016·Bioorganic & Medicinal Chemistry Letters·Mathieu MaingotJean-Alain Fehrentz
Jun 19, 2016·European Journal of Medicinal Chemistry·Sheng-Rong LiaoYonghong Liu
Apr 6, 2017·The Journal of Antibiotics·Mingwei SunYuemao Shen

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Citations

May 21, 2020·Chemical Communications : Chem Comm·Hannah L StewartDavid R Spring

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