One pot synthesis of polycyclic oxygen aromatics. Part III Mechanism of formation

Kasturi, T. R. ; Mandal, A. B. ; Amruta Reddy, P. ; Ganesha Prasad, K. B. ; Rajasekhar, B. (1991) One pot synthesis of polycyclic oxygen aromatics. Part III Mechanism of formation Tetrahedron, 47 (28). pp. 5245-5258. ISSN 0040-4020

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Reaction of 6-tert -butyl-1-bromomethyl-2-(2-tetrahydropyranyloxy)-naphthalene 2c with tetrachlorocatechol (TCC) in acetone in presence of K2CO3 gave diastereomers 6c and 7c. A mechanism (Scheme-1) invoking the base induced cleavage of the pyranyl ether 2 to 1,2-naphthoquinone-1-methide 8 as the first step has been postulated. The cleavage of the pyranyl ether linkage in 2 to give dimers 4 and 5 of 1,2-naphthoquinone-1-methide has been demonstrated with different bases. 1,2-Naphthoquinone-1-methide 8, thus generated, undergoes Michael addition with TCC followed by elimination of chloride ions to give a diketone, which further undergoes aldolisation with acetone to give diastereomers 6 and 7. Michael reaction of 8, generated in situ from pyranyl ethers 2a-c, with tetrabromocatechol (TBC) under similar-reaction conditions gave the expected monobromo compounds 6h, 6i, 6k, 7n, 7n and 7q. The last step in the proposed mechanism, viz., aldolisation has also been demonstrated using different ketonic solvents. Thus, reaction of 2a-c with TCC/TBC in diethyl ketone/methyl ethyl ketone under similar reaction conditions gave the expected compounds 6 and 7.

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