One pot synthesis of polycyclic oxygen aromatics

Kasturi, T. R. ; Amruta Reddy, P. ; Mandal, A. B. ; Sivaramakrishnan, R. ; Rajasekhar, B. ; Ganesha Prasad, K. B. ; Radhakrishnan, R. ; Viswamitra, M. A. (1990) One pot synthesis of polycyclic oxygen aromatics Tetrahedron, 46 (20). pp. 7047-7058. ISSN 0040-4020

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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 ±cis - trans and -8-chloro-10-hydroxy-10-(2-oxopropyl) spiro [11 H̲ -benzo[a̲] xanthen-ll2'(1'H̲) naphtho [21-b̲ furan]-9 (1O H̲ -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:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:16139
Deposited On:15 Nov 2010 14:07
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