Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones

被引：3

作者：

Malcor, Jean-Daniel

Brouillette, Yann

Graffion, Julien

Spielmann, Kim

Masurier, Nicolas

Maillard, Ludovic T.

Martinez, Jean

Lisowski, Vincent ^{[1
]}

机构：

[1] Univ Montpellier I, CNRS, Inst Biomol Max Mousseron, UMR 5247, F-34093 Montpellier, France

来源：

TETRAHEDRON | 2014年 / 70卷 / 31期

关键词：

Pyrrolo[d]oxazine-2,4-dione; Pyrrolodiazepine-2,5-dione; Diazepines; Imidazolidine-2,4-dione; 3-Aminopyrrole derivatives; SOLID-PHASE SYNTHESIS; THIAISATOIC ANHYDRIDES; EFFICIENT SYNTHESIS; RING-SYSTEM; AGENTS; ANALOGS; ACID; DERIVATIVES; INHIBITORS; ANTAGONISTS;

D O I：

10.1016/j.tet.2014.05.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient synthesis of pyrrolo[3,2-d][1,3]oxazine-2,4-dione 4 is described and its reactivity towards various nucleophiles studied. The regioselective ring opening of anhydride 4 or its N-alkylated analog 25 in the presence of alanine or proline afforded, respectively, imidazolidinedione 22 and N-protected pyrrolo[3,2-e][1,4]diazepines 30 and 31 in a one-pot process. In a last part of this study, an alternative route to produce a library of eight non protected pyrrolo[3,2-e][1,4]diazepine-2,5-diones 35a-h is described to overcome the limited reactivity of anhydride 4. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4631 / 4639

页数：9

共 48 条

[1] Design, synthesis and preliminary evaluation of some novel [1,4]diazepino [5,6-b]pyrrolizine and 6-(2-oxopyrrolidino)-1H-pyrrolizine derivatives as anticonvulsant agents [J].