Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

Juan F. González; Irene Ortín; Elena de la Cuesta; J. Carlos Menéndez

doi:10.1039/C2CS35158G

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Chemical Society Reviews

Issue 21, 2012

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Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

Juan F. González,^a Irene Ortín,^a Elena de la Cuesta^a and J. Carlos Menéndez*^a

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Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain
E-mail: josecm@farm.ucm.es ;
Fax: +34 91 3941822 ;
Tel: +34 91 3941840

Chem. Soc. Rev., 2012,41, 6902-6915

DOI: 10.1039/C2CS35158G
Received 25 Apr 2012, First published online 25 Jul 2012

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Abstract
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2,5-Piperazinediones (2,5-diketopiperazines, DKPs) can be viewed as privileged building blocks for the synthesis of heterocyclic systems. This tutorial review aims at underscoring the large number and structural variety of nitrogen heterocycles that are available by suitable manipulation of DKP starting materials, including many bioactive compounds and natural products.

Abstract from Methods in Organic Synthesis 2013

A tutorial review, with 53 references, of 2,5-piperazidones as starting materials for the synthesis of heterocycles. Transformations of the system via reactions of the carbonyl groups, ring opening, aza-Wittig reactions, condensations, Dieckmann cyclisations, reductions, Heck reactions, Pictet–Spengler reactions, alkylations, arylations, rearrangements etc. deliver a large variety of heterocyclic compounds with biological or pharmacological significance.

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Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

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