A highly regio- and stereoselective synthesis of (Zâ )-3-arylidene-2,3-dihydro-5H-1,4-benzodioxepin-5-ones and (Zâ )-3-arylidene-1,2,3,5-tetrahydro-4,1-benzoxazepin-5-ones through palladiumâ copper catalysis
Chaudhuri, Gopeswar; Kundu, Nitya G.; Chaudhuri Gopeswar; Department of Organic Chemistry, Indian Association for the Cultivation of Science; Kundu Nitya G.; Department of Organic Chemistry, Indian Association for the Cultivation of Science
Журнал:
Journal of the Chemical Society, Perkin Transactions 1
Дата:
2000
Аннотация:
Sodium 2-(prop-2â ²-ynyloxy)benzoate 1a reacted with the aryl iodides 2â 10 in the presence of bis(triphenylphosphine)palladium(II) chloride, cuprous iodide and triethylamine in CH3CNâ DMF to yield the disubstituted alkynes 11â 19 in good yields (48â 58%). Similarly, sodium 2-[N-benzyl-N-(prop-2â ²-ynyl)]aminobenzoate 1b on reaction with aryl iodides under palladiumâ copper catalysis afforded the disubstituted alkynes 20â 22. Compounds 11â 19 on cyclisation with cuprous iodide in the presence of triethylamine in acetonitrile yielded the 3-arylidene-2,3-dihydro-5H-1,4-benzodioxepin-5-ones 23â 31 in 61â 83% yields. Similarly, compounds 20â 22 on cyclisation gave 3-arylidene-1,2,3,5-tetrahydro-4,1-benzoxazepin-5-ones 32â 34.
114.9Кб