Synthetic entry to dibenzo [b, f] oxinin and dibenzo [b, f] azonine derivatives through a dibenzo [a, e] cycloocten-5-one
IW Elliott, MJ Sloan, E Tate
Index: Elliott, I. Wesley; Sloan, Milton J.; Tate, Earl Tetrahedron, 1996 , vol. 52, # 24 p. 8063 - 8072
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Citation Number: 8
Abstract
2, 3, 8, 9-Tetramethoxy-5, 6, 11, 12-tetrahydrodibenzo [a, e] cycloocten-5-one (2) was transformed by Baeyer-Villiger oxidation to the substituted 6-oxodibenzo [b, f] oxinin 6. One- pot Beckmann or Schmidt rearrangements of 2 afforded the 6-oxodibenzo [b, f]-azonine 8 which was reduced by BH3-THF to the tricyclic amine 14. Parallel reactions with desoxyveratroin gave the ester 7 or amide 12 from preferential migration of the 3, 4- ...
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