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 Citations (Scopus)

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 2014

Fingerprint

Nucleophiles
Diamines
Cyclization
Scaffolds
Purification
Condensation
Amino Acids
Acids
glyoxylic acid

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Expeditious routes to polycyclic molecular frameworks via one-pot, two-step Ugi ring-closing sequences. / Xu, Zhigang; De Moliner, Fabio; Cappelli, Alexandra P.; Ayaz, Muhammed; Hulme, Christopher.

In: Synlett, Vol. 25, No. 2, ST-2013-D0922-L, 01.2014, p. 225-228.

Research output: Contribution to journalArticle

Xu, Zhigang ; De Moliner, Fabio ; Cappelli, Alexandra P. ; Ayaz, Muhammed ; Hulme, Christopher. / Expeditious routes to polycyclic molecular frameworks via one-pot, two-step Ugi ring-closing sequences. In: Synlett. 2014 ; Vol. 25, No. 2. pp. 225-228.
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