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2004
Alkaloids
U 0600
45- 218
Pictet—Spengler-Type Reactions in 3-Arylmethylpiperazine-2,5-diones. Synthesis of Pyrazinotetrahydroisoquinolines. — Paraformaldehyde and benzaldehyde
acetals undergo N-alkylation of 3-arylmethylpiperazine-2,5-diones such as (I) to give
alcohols or amidoacetals, which undergo Pictet—Spengler-type cyclizations to give the
tricycles shown. When the N-alkylation and cyclization steps are carried out in a
one-step procedure [→ (XIV)], the N-acetyl substituent which is needed to give anchimerical assistance in the synthesis of some bioactive pyrazinoisoquinoline compounds
is cleaved. — (GONZALEZ, J. F.; DE LA CUESTA, E.; AVENDANO*, C.;
Tetrahedron 60 (2004) 30, 6319-6326; Dep. Quim. Org. Farm., Fac. Farm., Univ.
Complutense, E-28040 Madrid, Spain; Eng.) — Kieslich
2004
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