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1 article(s) from Grzelak, Paulina

Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

Grzegorz Mlostoń,
Paulina Grzelak,
Maciej Mikina,
Anthony Linden and
Heinz Heimgartner

Beilstein J. Org. Chem. 2015, 11, 576–582, doi:10.3762/bjoc.11.63

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Scheme 1: Hetero-Diels–Alder reaction of thiobenzophenone (1a) with dimethyl acetylenedicarboxylate (2a) [10].

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Scheme 2: Synthesis of polycyclic thiopyrans via the hetero-Diels–Alder reaction/1,3-hydrogen shift sequence.

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Figure 1: ORTEP Plot [19] of the molecular structure of 4b, drawn using 50% probability displacement ellipsoids.

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Scheme 3: Reactions of aryl/hetaryl thioketones with methyl propiolate (Table 1).

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Scheme 4: Oxidation of selected thiopyrans 4 and 5 to give the corresponding sulfones.

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Figure 2: ORTEP Plot [19] of the molecular structure of one of the symmetry-independent molecules of 6d, drawn us...

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Published 28 Apr 2015

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