From ascorbigens to indolocarbazoles

Add time:07/13/2019    Source:sciencedirect.com

New methods of l-ascorbic acid derivatization with the use of polyfunctional indole-3-cabinols are described. Reaction of β-hydroxy-N-methyltryptamine and l-ascorbic acid gave lactame derivatives; (indol-3-yl)glycolic and l-ascorbic acids produced 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)-cyclopen-2-enone. Similarly, 4-hydroxy-3-methoxyphenylglycolic and l-ascorbic acids yielded 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-4-hydroxymethyl-cyclopen-2-enone. Properties of N-methoxyascorbigen (neoascorbigen) were investigated. Alkylation of l-ascorbic acid with polysubstituted pyrrolecarbinols led to pyrrole analogues of ascorbigen. Acidic transformation of 3-formylindole and 1-methyl-3-formylindole led to indolocarbazoles and triindolylmethane derivatives.

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