Synthesis, structure and unusual reactivity of a stable 3-(oxazolidin-2-ylidene)thiophen-2-one

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3 Citations (Scopus)

Abstract

Treatment of 2- and 3-thienyloxazolines with butyllithium and bis(trimethylsilyl) peroxide results in ring hydroxylation to give products which exist mainly as the oxazolidinylidenethiophenones. The 3-oxazolidinylidenethiophen-2-one is a rare example of a stable heterocyclic ortho-quinone methide analog which shows a varied pattern of reactivity, including both C- and O-alkylation, Michael addition via C-5 to an acetylenic ester, tetrachlorobenzannulation across positions 4 and 5, and formation of a hexacyclic fused-ring product with N-phenyltriazolinedione. Crystal structures of the products are dominated by inter- and intramolecular NH to CO hydrogen bonding.
Original languageEnglish
Pages (from-to)10527-10531
Number of pages5
JournalThe Journal of Organic Chemistry
Volume81
Issue number21
Early online date15 Jul 2016
DOIs
Publication statusPublished - 4 Nov 2016

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