Tandem hetero-Diels-Alder-hemiacetal reaction in the synthesis of new chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles

Abstract

Novel rel-(5aR,6R,11bS)-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-ones were synthesized via tandem hetero-Diels-Alder-hemiacetal reaction of 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones and α,β-unsaturated aldehydes. The stereochemistry of cycloadditions was confirmed by NMR spectra and a single crystal X-ray diffraction analysis.