Abstract
Trimethyl orthoacetate was found to be a convenient reagent for methylation of the β-OH groups of (poly)hydroxynaphthazarins. The substrates bearing one β-OH group react with MeC(OMe)3 to give the corresponding methoxy derivatives in 79–89% yields. Depending on the reaction conditions, methylation of substrates with two β-OH groups on the different and the same rings affords either the corresponding mono-O-methylated (43–70%) or di-Omethylated (71–78%) derivatives. Trimethyl orthoacetate offers a good alternative to CH2N2 in the preparative synthesis of O-methylated (poly)hydroxynaphthazarin derivatives.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0055–0063, January, 2019.
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Balaneva, N.N., Shestak, O.P. & Novikov, V.L. Trimethyl orthoacetate as a convenient reagent for selective methylation of β-OH groups of (poly)hydroxynaphthazarins. Russ Chem Bull 68, 55–63 (2019). https://doi.org/10.1007/s11172-019-2415-5
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DOI: https://doi.org/10.1007/s11172-019-2415-5