A modular CuI-L-proline catalyzed one-pot route for the rapid access of constrained and privileged hetero-atom-linked medium-sized ring systems

Vunnam Srinivasulu, Kim D. Janda, Imad A. Abu-Yousef, Matthew John O'Connor, Taleb H. Al-Tel

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient CuI-L-proline catalyzed one-pot synthesis was developed to generate a collection of skeletally diverse heterocyclic ring systems with sizes ranging from 6 to 9. A salient feature of this design strategy is its modular synthetic utility using an SN2 reaction followed by a microwave assisted CuI-L-proline hetero-arylation, which has granted access to a series of heterocyclic frameworks including: benzo[e]pyrrolo[1,2-a][1,4]diazepin, benzo[e]pyrrolo[1,2-a][1,4]diazocin, benzo[e]pyrido[1,2-a][1,4]diazocinones, dibenzo[b,f][1,5]diazoninones, dihydrodibenzo[b,e][1,4]thiazepine, dibenzo[b,e][1,4]thiazocine and benzo[6,7][1,4]diazepino[1,2-a]indole. Moreover, the synthetic procedures described herein, allows rapid entries to synthetically challenging medium-sized heterocyclic systems with good overall yields.

Original languageEnglish (US)
Pages (from-to)2139-2150
Number of pages12
JournalTetrahedron
Volume73
Issue number15
DOIs
StatePublished - 2017

Keywords

  • CuI-L-proline Catalyst
  • Diversity oriented synthesis
  • Fused tricyclic N-heterocycles
  • Medium ring systems
  • One-pot synthesis
  • Priviledged structures
  • S2/hetero-annulation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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