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-l,2,4-triol to give the (€) -3,6-dihydroxy-2methyl-I ,4benzoquinone 4-methoxyimine N-oxide is noted. A novel indole formation is described.

Benzoquinones from millipedes deter mosquitoes and elicit self-anointing in capuchin monkeys ( Cebus spp.)

“…MMB was synthesized from 2 0 ,4 0 -dihydroxy-3 0 -methylacetophenone (Sigma-Aldrich) via 4 0 -benzyl-2 0 -methoxy-3 0 -methylacetophenone (Raphael and Ravenscroft 1998). BaeyerVilliger oxidation with m-chloroperoxybenzoic acid in the presence of toluenesulfonic acid (Knölker and Fröhner 1997) gave the acetate of 4-benzyloxy-2-methoxy-3-methylphenol.…”

A catalytic method for synthesis of γ-butyrolactone, ɛ-caprolactone and 2-cumaranone in the presence of Preyssler's anion, [NaP5W30O110]14−, as a green and reusable catalyst

“…Lactones of five, and larger rings, are of interest because of their applications in building up biologically active compounds which exhibit various pharmacological activities [1][2][3][4][5]. They can be also used for the synthesis of polyesters [6,7].…”

One-Pot Synthesis of α-Alkylidene-γ-butyrolacton-2-ones (Tetronic Acid Derivatives): Polar Solvent Induces a New Type of γ-Lactonization

“…[1][2][3][4][5] They are commonly known for their cytostatic and antimicrobial 6,7 activity. Many of them have feeding deterrent activity against insects.…”