Abstract
Haloindenes are convenient precursors in organic
and biologically targeted syntheses. Although there are several reports for
the synthesis of 5- or 6-chloro- and bromoindenes, there is only one method for
the preparation of more reactive 5- or 6-iodoindene which requires expensive
intermediates and several steps. Furthermore, reported yields for 5- or
6-iodoindenes obtained by the reduction of the corresponding 5- or
6-nitroindene followed by diazotization-iodination of the resulting unstable 5-
or 6-aminoindene were only 20% and 7%. FIU inventors have developed expedited synthesis of 5, 6, and
7-iodoindenes from the corresponding aminoindan-1-ones in more than 70% yield,
employing readily available precursors and reagents. A three-step sequence
involves diazotization-iodination of 5 aminoindan-1-one followed by reduction
and dehydration. The method has a general character and can be extended for the
preparation of various 4-, 5-, 6- or 7-haloindenes using different halogen
sources for diazotization-halogenation reaction.
Benefit
Preparation of expensive 5-iodoindene and unreported 7-iodoindene in high yields utilizing readily available and cost-effective reagentsAvoids the use of expensive nitroindenes, unstable aminoindenes, and potentially explosive trifluoroperacetic acidCan be extended for the preparation of various 4-, 5-, 6- or 7-haloindenes
Market Application
Precursors in organic and biologically targeted syntheses
Publications
A. Hasan Howlader, Keili Diaz, Alexander M. Mebel, Ralf I. Kaiser,
Stanislaw F. Wnuk, Iodoindenes: Synthesis and application to cross-coupling, Tetrahedron
Letters, Volume 61, Issue 43, 2020, 152427, ISSN 0040-4039
Brochure
