- Dichlorodicyanoquinone Oxidations in the Indole Area. Synthesis of Crenatine
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The influence of temperature on the reaction of dichlorodicyanoquinone (DDQ) with 1,2,3,4-tetrahydro-β-carbolines has been explored.The DDQ oxidation of amide 2a, when performed at room temperature, gave 3a (3-acylindole)/4 (2-acylindole) in a ratio of ca. 1:1, while this was increased to 2:1 at 0 deg C and to ca. 5:1 at -78 deg C.This method for preparation of 4-oxo-β-carbolines has been employed for synthesis of the β-carboline alkaloid crenatine (11).In addition, treatment of the 4-oxotetrahydro-β-carboline (3b) with hydrazine gave 1-ethyl-4-amino-β-carboline (12) which should provide access to a series of 4-substituted β-carbolines.
- Cain, M.,Mantei, R.,Cook, J. M.
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p. 4933 - 4936
(2007/10/02)
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- SELENIUM DIOXIDE OXIDATIONS IN THE β-CARBOLINE AREA
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The reaction of 1-ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 11 with selenium dioxide has resulted in the synthesis of the β-carboline alkaloids, 1-acetyl-3-methoxycarbonyl-β-carboline 14 and 1-acetyl-β-carboline 15.Application of this technol
- Campos, Olivia,DiPierro, Mike,Cain, Michael,Mantei, Robert,Gawish, Ali,Cook, James M.
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p. 975 - 984
(2007/10/02)
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