A convenient synthesis of dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates by one carbon extension. Issue 26 (24th June 2015)

• Record Type: Journal Article
• Authors: Sathishkumar, S.; Mahasampathgowri, S.; Balasubramanian, K.K.; Saiganesh, R.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 26(2015)
• Page Start: 4031
• Page End: 4035
• Publication Date: 2015-06-24
• Subjects: Sulfoxonium ylide -- DIMSOY -- One carbon extension -- 2-Haloethylidenemalonates -- Halocrotonates; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.015
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 2-Haloethylidenemalonates are highly reactive species and useful synthons for the synthesis of Famvir®, an antiviral drug. Simple methods for the preparation of 2-haloalkylidenemalonates are not available. We have developed a novel and non-cumbersome methodology for the synthesis of dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates by one carbon extension of dialkyl (2-alkoxymethylene)malonates, cyanoacetates and 3-alkoxyacrylates with dimethylsulfoxonium methylide.