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One pot synthesis of polycyclic oxygen aromatics

Kasturi, TR and Reddy, Amruta P and Mandal, AB and Sivaramakrishnan, R and Rajasekhar, B and Ganesha Prasad, KB and Radhakrishnan, R and Viswamitra, MA (1990) One pot synthesis of polycyclic oxygen aromatics. In: Tetrahedron, 46 (20). pp. 7047-7058.

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Reaction of 1-bromomethyl-2-(2-tetrahydropyranyloxy) naphthalene (5a) with tetrachlorocatechol in acetone in presence of anhydrous potassium carbonate resulted in the formation of compounds 7a 8a and 9a along with diastereomeric products to which $\pm\hspace{1mm} cis$ and $trans$-8-chloro-10-hydroxy-10-(2-oxopropyl) spiro [11$H$-benzo$[a]$xanthen-ll2'(1'$H$ naphtho [21-$b$ furan]-9 (1O$H$-one (13a and l4a) structures were assigned based on spectral data. Similar reaction of the corresponding bromo compound (5b) using acetone or diethyl ketone as solvent gave the corresponding diastereomeric pair of compounds (13 and 14). X-ray crystal structure analysis of one of the $trans$ compounds 14c further confirmed the assigned structure

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Pergamon Press plc.
Additional Information: Copyright of this article belongs to Pergamon Press plc.
Keywords: polycyclic oxygen aromatics;anhydrous potassium carbonate
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Division of Physical & Mathematical Sciences > Physics
Date Deposited: 17 Dec 2007
Last Modified: 19 Sep 2010 04:41
URI: http://eprints.iisc.ac.in/id/eprint/12500

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