Synthesis of indolin-2-ones (oxindoles) related to mitomycin A
Abstract
Oxindoles (Indolin-2-ones) containing the functionality of the first two rings of the mitomycin A structure have been synthesized. Attempts to employ the oxindole grouping to construct the third ring were unsuccessful because of the resistance of the oxindole group or its derivatives towards nucleophilic attack. An unusual methylation of 3-methyl-5-nitrobenzene-1,2,4-triol to give the (E)-3,6-dihydroxy-2-methyl-1,4-benzoquinone 4-methoxyimine N-oxide is noted. A novel indole formation is described.