Synthesis and reactivity of furoquinolines bearing an external methylene-bond: access to reduced and spirocyclic structures

Org Biomol Chem. 2011 Jul 7;9(13):4831-41. doi: 10.1039/c1ob05354j. Epub 2011 May 5.

Abstract

A family of furoquinolines were efficiently obtained through a tandem acetalization/cycloisomerization process catalyzed by (5 mol%) silver imidazolate polymer and triphenylphosphine, and diversity was brought by the use of 7 different alcohol groups. From these furoquinolines, 3 examples of reduced derivatives could be obtained (d.r. up to 94 : 6), 10 different spiroketal derivatives by hetero-Diels-Alder reaction (d.r. up to 20 : 1), 8 hetero-[5,5]-spirocycles by cycloaddition with dibromoformaldoxime (d.r. up to 86 : 14) and finally 6 hetero-[5,6]-spirocycles by [4 + 2] cycloaddition with ethyl 3-bromo-2-(hydroxyimino)propanoate (d.r. up to 90 : 10).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Methane / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Quinolones / chemical synthesis*
  • Spiro Compounds / chemical synthesis*

Substances

  • Quinolones
  • Spiro Compounds
  • Methane