Some aspects of the chemistry of 6,7,8,9-tetrahydro-3-hydroxy-2-methoxybenzocycloheptan-5-one

Abstract

6,7,8,9-Tetrahydro-3-hydroxy-2-methoxybenzocyclohepten-5-one has been converted into several bromoderivatives, acetals, and esters, and into 3-hydroxy-2-methoxybenzocyclohepten-5-one; further, its reduction with LiAlH₄ has been compared with that of 6,7-dihydro-3-hydroxy-2-methoxybenzocyclohepten-5-one. A synthesis of 6,7-dihydro-3-hydroxy-8-hydroxycarbonyl-2-methoxybenzocyclohepten-5-one has been developed. Synthesis of 6,7,8,9-tetrahydro-4-methoxy-10H-cyclohepta[e]benzofuran-10-ones, 9-hydroxy-5,6-dihydro-8-methoxy-4H-benzo[6,7]cyclohept[1,2-c]pyrazole, 5,6-dihydro-9-hydroxy-8-methoxy-4H-benzo[3,4]cyclohept[1,2-d]isoxazole, and 10-hydroxy-6,7-dihydro-9-methoxybenzo[5,6]cyclohept[1,2-b]indole are described.