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Beilstein J. Org. Chem. 2015, 11, 576–582, doi:10.3762/bjoc.11.63
Graphical Abstract
Scheme 1: Hetero-Diels–Alder reaction of thiobenzophenone (1a) with dimethyl acetylenedicarboxylate (2a) [10].
Scheme 2: Synthesis of polycyclic thiopyrans via the hetero-Diels–Alder reaction/1,3-hydrogen shift sequence.
Figure 1: ORTEP Plot [19] of the molecular structure of 4b, drawn using 50% probability displacement ellipsoids.
Scheme 3: Reactions of aryl/hetaryl thioketones with methyl propiolate (Table 1).
Scheme 4: Oxidation of selected thiopyrans 4 and 5 to give the corresponding sulfones.
Figure 2: ORTEP Plot [19] of the molecular structure of one of the symmetry-independent molecules of 6d, drawn us...