Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones |
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Authors: | Tarun Kanti Pradhan Jacques Mortier |
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Institution: | a Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 072, India b Unité de Chimie organique moléculaire et macromoléculaire, Faculté des sciences et techniques, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France |
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Abstract: | Chemoselective synthesis of thioaurones or 3-hydroxy benzob]thiophen-2-aryl ketones, 1-hydroxy naphtho2,1-b]thiophen-2-aryl ketones and chalcones from N,N-diethyl-ortho-methyl sulfanyl aryl amides were described. (Benzob]thiophen-2-yl) alkylates and (naphtho2,1-b]thiophen-2-yl) alkylates undergo a novel anionic ortho-Fries rearrangement leading to (3-hydroxy benzob]thiophen-2-yl) and (1-hydroxy naphtho2,1-b]thiophen-2-yl) alkyl ketones. The hydroxy ketones were used as intermediates in the synthesis of wide range of benzothienopyranones and thiafluorenones. |
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Keywords: | Directed metalation Chemoselectivity Thioaurones Chalcone Anionic ortho-Fries rearrangement Benzothienopyranone |
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