Intramolecular electrophilic hydroarylation via Claisen rearrangement: synthesis of chromenes, heterothiochromenes and heterodihydrothiochromenes

We have designed and synthesized several basic and novel fused ring heterocycles by intramolecular hydroarylation with an efficiency and scope to develop intermediates of potential value. This method demonstrated consistent performance with arene–ene and arene–yne substrates of diverse structural fe...

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Bibliographic Details
Published in:Tetrahedron 2006-09, Vol.62 (39), p.9280-9288
Main Authors: Kenny, Rajesh S., Mashelkar, Uday C., Rane, Deepak M., Bezawada, Dinesh K.
Format: Article
Language:English
Subjects:
Chromene
Claisen rearrangement
Dihydrothiopyran
Hydroarylation
Pyran
Thiopyran
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Summary:We have designed and synthesized several basic and novel fused ring heterocycles by intramolecular hydroarylation with an efficiency and scope to develop intermediates of potential value. This method demonstrated consistent performance with arene–ene and arene–yne substrates of diverse structural features, including propargyl ethers, allyl thioethers, and propargyl thioethers resulting in 6- endo products. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.06.079