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Fernández, E. et al.: 2021 Science of Synthesis, 2021/2: Knowledge Updates 2021/2 DOI: 10.1055/sos-SD-140-00314
Knowledge Updates 2021/2

40.1.8 Product Subclass 8: Piperazines

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Book

Editors: Fernández, E.; Huang, Z.; Jiang, X.; Koch, G.; Marschner, C.; Wang, M.

Authors: Chand, K. ; Davies, G. H. M.; Dorairaj, D. P.; Guo, R.; Hsu, S. C. N. ; Isovitsch, R.; Jiang, X.; Růžička, A.; Sirvinskas, M.; Takeda, N.; Trofimova, A.; Umesh; Vrána, J.; Wang, M.; Wisniewski, S. R.; Xiong, Y.; Ye, Z.-S.; Yudin, A. K.; Zhang, G. Z. 

Title: Knowledge Updates 2021/2

Print ISBN: 9783132442061; Online ISBN: 9783132442085; Book DOI: 10.1055/b000000477

1st edition © 2021 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

The piperazine unit is widely distributed in natural products and life-saving small-molecule pharmaceuticals. It is the third most common nitrogen heterocycle occurring in pharmaceuticals approved by the U. S. Food and Drug Administration. This chapter covers strategies for the synthesis and transformations of piperazines, with both classical methods and recent developments reviewed. A major focus is on cyclization reactions such as intramolecular hydroaminations, multicomponent approaches, and routes from ethane-1,2-diamine substrates. Also discussed are approaches based on hydrogenation of (hydro)pyrazines by heterogeneous catalysis and by (asymmetric) homogeneous catalysis. Finally, a variety of transformations involving modification of a substituent on a piperazine ring are surveyed, including arylations, alkylations, and oxidations.

Key words

piperazines - cyclization - hydroamination - Ugi reaction - allylation - arylation - hydrogenation - dearomatization - asymmetric synthesis - lithiation - activation of C-H bonds - cross-coupling reactions
 
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