Expeditious routes to polycyclic molecular frameworks via one-pot, two-step Ugi ring-closing sequences

Zhigang Xu, Fabio De Moliner, Alexandra P. Cappelli, Muhammed Ayaz, Christopher Hulme

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

A very general and robust multicomponent-reaction protocol involving an Ugi condensation between ethyl glyoxylate, isonitriles, N-Boc-α-amino acids, and mono-N-Boc-protected diamines followed by a series of acid-promoted cyclization steps in a one-pot fashion is reported. This process allows for the assembly of complex polycyclic structures by means of just two simple synthetic operations and a single chromatographic purification in high overall yields. Of note, the first scaffolds derived from a highly Âselective sequence of ring-closing events involving three internal amino nucleophiles is reported.

Original languageEnglish (US)
Article numberST-2013-D0922-L
Pages (from-to)225-228
Number of pages4
JournalSynlett
Volume25
Issue number2
DOIs
StatePublished - Jan 1 2014

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Keywords

  • heterocycles
  • isonitriles
  • multicomponent reaction
  • nucleophilic attack
  • one-pot process

ASJC Scopus subject areas

  • Organic Chemistry

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