Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 8, pp. 1489−1493.
Pleiades Publishing, Ltd., 2010.
Original Russian Text
A.V. Kharitonova, A.A. Gorbunov, Yu.V. Shklyaev, 2010, published in Zhurnal Prikladnoi Khimii, 2010, Vol. 83, No. 8, pp. 1383−1387.
Mandelonitrile in Synthesis of Partially Hydrogenated
A. V. Kharitonova, A. A. Gorbunov, and Yu. V. Shklyaev
Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm, Russia
Received March 10, 2010
Abstract—New procedures for preparing tetrahydroisoquinoline derivatives using available chemicals are
1,2,3,4-Tetrahydroisoquinoline (THIQ) derivatives
widely occur in the nature and exhibit high pharmacological
activity [1–3]. The most widely used route of their
synthesis is the Pictet–Spengler reaction . With the aim
to develop new routes to THIQ derivatives and expand
the range of chemicals suitable for their synthesis, we
performed a three-component reaction of mandelonitrile,
isobutyraldehyde, and activated arenes. We expected
that the reaction of mandelonitrile, isobutyraldehyde,
and veratrole would yield 1-benzoyl-6,7-dimethoxy-
3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 1a owing
to imine–enamine tautomerism in intermediate A and
transformation of the hydroxy group at the double bound
into keto group (Scheme 1).
We found that the reaction performed with freshly
prepared mandelonitrile yielded an equimolar mixture of
1(2Н)-ylidene](phenyl)methanol 1 and 1-benzoyl-6,7-
dimethoxy-3,3-dimethyl-3,4-dihydroisoquinoline 2. The
physicochemical constants of 2 fully agree with those
reported in . Apparently, product 2 originates from
oxidation of the intermediate 3,3-dialkyl-6,7-dimethoxy-