Jump to main content
Jump to site search

Issue 10, 2011
Previous Article Next Article

Synthesis of spirocyclic thiazolidinediones using ring-closing metathesis and one-pot sequential ring-closing/cross metathesis

Author affiliations

Abstract

A novel synthetic route to spirocyclic thiazolidinediones is reported by utilizing ring-closing metathesis (RCM). A selective cross metathesis (CM) of N-allyl azaspiro derivatives with different olefins has been demonstrated to prepare substituted azaspiro-[4.4]nonenediones. The X-ray crystal structure of a spirocyclic thiazolidinedione dimer is described, which has been prepared in two steps from thiazolidinedione using a one-pot sequential ring-closing and self metathesis. Cross metathesis proceeds smoothly with both electron rich and poor olefins. The symmetrical bis-thiazolidinedione spirocyclic system can be used as CM coupling partner with olefins. One-pot sequential RCM-CM has been developed for the synthesis of substituted spirocyclic compounds. The methodology allows a quick access to thia-azaspiro-[4.4]nonene and -[4.5]decene-dione ring systems from readily available starting materials which are not otherwise accessible.

Graphical abstract: Synthesis of spirocyclic thiazolidinediones using ring-closing metathesis and one-pot sequential ring-closing/cross metathesis

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Dec 2010, accepted on 23 Feb 2011 and first published on 24 Feb 2011


Article type: Paper
DOI: 10.1039/C0OB01248C
Citation: Org. Biomol. Chem., 2011,9, 3801-3807
  •   Request permissions

    Synthesis of spirocyclic thiazolidinediones using ring-closing metathesis and one-pot sequential ring-closing/cross metathesis

    K. Dhara, S. Paladhi, G. C. Midya and J. Dash, Org. Biomol. Chem., 2011, 9, 3801
    DOI: 10.1039/C0OB01248C

Search articles by author

Spotlight

Advertisements