Abstract: The spontaneous conversion of 3-indoxyl to indigo was a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids.
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2-(7-methyl-1H-indol-3-ylthio)-6-(difluoromethoxy)-1hbenzo[d]imidazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
With manganese(III) triacetate dihydrate; acetic acid; at 80℃; for 2h;Inert atmosphere;
General procedure: Manganese triacetate (2 mmol) is added portion wise to a pre dissolved solution of Indole (1mmol) and benzimidazolethiol (1mmol) in acetic acid (10mL) at room temperature under Nitrogen atmosphere. The reaction mixture is stirred at 80 C for 2 hours. After completion of reaction, as monitored by T.L.C analysis, the reaction mixture was quenched by the addition of water 20 ml. The organic compounds are extracted with ethyl acetate (3x20ml). The combined layers are dried over anh.Na2SO4. The required product is purified by column chromatography, eluted with 8% methanol in DCM to get the product. The product is confirmed by 1H, 13C, NMR, IR and mass
Chemistry
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Material Science
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120K+ Compounds
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