Anhydride-Based Multicomponent Reactions

Kevin S. Martin, Jared T. Shaw, Ashkaan Younai

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

Anhydrides are increasingly important building blocks in the advent of new multicomponent reactions (MCRs). Their unique ability to serve as mild acylating agents that can also engage in conjugate addition, cycloaddition, and nucleophilic addition processes enables them to participate in a wide variety of one-pot cascade reactions. This chapter gives an overview of reactivity trends that have enabled the development of anhydride-based MCRs. Homophthalic and isatoic anhydrides have dual reactivity that is well suited to MCRs. The chapter presents examples of MCRs involving cyclic anhydrides that involve both carbonyl groups being incorporated into the scaffold formed during the reaction process. However, acyclic anhydrides (such as acetic anhydride) have been used in a variety of domino multicomponent processes as a means to capping newly formed alcohol and amine functionalities in situ.

Original languageEnglish (US)
Title of host publicationMulticomponent Reactions in Organic Synthesis
PublisherWiley Blackwell
Pages379-400
Number of pages22
ISBN (Print)9783527678174, 9783527332373
DOIs
StatePublished - Feb 9 2015

Keywords

  • Acyclic anhydrides
  • Cyclic anhydrides
  • Homophthalic anhydrides
  • Isatoic anhydrides
  • Multicomponent reactions (MCRs)

ASJC Scopus subject areas

  • Chemistry(all)

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  • Cite this

    Martin, K. S., Shaw, J. T., & Younai, A. (2015). Anhydride-Based Multicomponent Reactions. In Multicomponent Reactions in Organic Synthesis (pp. 379-400). Wiley Blackwell. https://doi.org/10.1002/9783527678174.ch13