Pictet Spengler-type reactions in 3-arylmethylpiperazine-2,5-diones.: Synthesis of pyrazinotetrahydroisoquinolines

被引：30

作者：

González, JF ^{[1
]}

de la Cuesta, E ^{[1
]}

Avendaño, C ^{[1
]}

机构：

[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

来源：

TETRAHEDRON | 2004年 / 60卷 / 30期

关键词：

annulations acetals; electrophilic aromatic substitution; acyliminium cations;

D O I：

10.1016/j.tet.2004.05.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The behavior of aldehydes and acetals as N-alkylating agents of 1-acetyl-3-arylmethylpiperazine-2,5-diones and the subsequent cyclization of the N-alkylated products was studied. Use of paraforinaldehyde in different reaction conditions gave 6-unsubstituted 3,6,11,11a-tetrahydro-2H-pyrazino[1,2-b]isoquinoline-1,4-diones and, in some cases, benzo[f]pyrazino[1,2-c]1,3-oxazepine-1,4-diones. Successful reactions with benzaldehyde required a first activation of the lactam function and a catalyzed N-alkylation with the aldehyde dimethyl acetal. The isolated O,N-amidoacetals thus obtained were submitted to a diastereoselective Pictet Spengler-type reaction that worked with arenes at several degrees of ring activation and with thiophene to give 6-phenylpyrazinoisoquinolinediones and the corresponding thieno analog. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6319 / 6326

页数：8

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