Efficient synthesis and structural analysis of new dioxopiperazine isoquinolines

被引：9

作者：

Cabedo, N

El Aouad, N

Berenguer, I

Zamora, M

de Arellano, MCR

Suvire, F

Bermejo, A

Enriz, D

Cortes, D ^{[1
]}

机构：

[1] Univ Valencia, Fac Farm, Dept Farmacol, Lab Farmacognosia, E-46100 Burjassot, Valencia, Spain

[2] Univ Nacl San Luis, Dept Quim, RA-5700 San Luis, Argentina

[3] Univ Valencia, Fac Farm, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON | 2006年 / 62卷 / 18期

关键词：

dioxopiperazine isoquinolines; synthesis; Pictet-Spengler; x-ray; semiempirical (PM3); ab initio and DFT calculations;

D O I：

10.1016/j.tet.2006.02.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein the synthesis of new dioxopiperazine isoquinolines using the Pictet-Spengler cyclisation. Our synthetic strategy for the preparation of two new compounds (5, 6), with a tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione moiety was developed in only four steps. To understand better the crucial step of the synthesis reported here, theoretical calculations using semiempirical (PM3), ab initio and DFT cornputations were carried out on a reduced system model. The structure of chlorohydrate water solvate of tetrahydro (2-piperidinylethyl)-6H-pyrazino [1,2-b]isoquinoline-1,4-dione (6-HCI-2H(2)O) was determined by X-ray diffraction. Theoretical calculations (RHF/3-21G and RB3LYP/6-31G(d)) were also performed for compound 6 neutralised with a chloride ion. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4408 / 4418

页数：11

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