Three-Step Synthesis of (Thio)xanthene and Dibenzothiepine/Dibenzoxepine by an Intramolecular Mizoroki-Heck Reaction of Diaryl (Thio)Ethers

We present a novel three-step protocol for preparing xanthene/thioxanthene and dibenzothiepine/dibenzoxepine from readily available starting materials. The Mizoroki-Heck cyclization as the final step was optimized to afford full conversion of the corresponding diaryl (thio)ethers and furthermore to...

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Bibliographic Details
Published inSynlett no. 3; pp. 418 - 422
Main Authors Jepsen, Tue Heesgaard, Larsen, Mogens, Jorgensen, Morten, Nielsen, Mogens Brondsted
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
fused-ring systems
heterocycles
Heck reaction
THIEPIN
palladium
sulfur
ARYL
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Summary:We present a novel three-step protocol for preparing xanthene/thioxanthene and dibenzothiepine/dibenzoxepine from readily available starting materials. The Mizoroki-Heck cyclization as the final step was optimized to afford full conversion of the corresponding diaryl (thio)ethers and furthermore to achieve reasonably good selectivity between the 6-exo and the 7-endo products.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0031-1290317