Synthesis of novel isoindolone derivatives via cascade reactions. Contrasting diastereoselectivity under solution-phase vis-a-vis solvent-free ball-milling reaction conditions

被引：8

作者：

Sanchez-Antonio, Omar ^{[1
]}

Gonzalez-Olvera, Rodrigo ^{[2
]}

Aguilera-Cruz, Alejandro ^{[2
]}

Reyes-Ramirez, Adelfo ^{[2
]}

Juaristi, Eusebio ^{[1
,3
]}

机构：

[1] Ctr Invest & Estudios Avanzados, Ave IPN 2508, Ciudad De Mexico 07360, Mexico

[2] UNAM, Fac Estudios Super Zaragoza, Unidad Multidisciplinaria Invest Expt, Batalla 5 Mayo S-N Esquina Fuerte de Loreto, Ciudad De Mexico 09230, Mexico

[3] Colegio Nacl, Ctr Hist, Luis Gonzalez Obregon 23, Ciudad De Mexico 06020, Mexico

来源：

TETRAHEDRON | 2019年 / 75卷 / 45期

关键词：

Michaelialdol-like cascade cyclization reaction; Isoindolones; Solvent-free ball-milling; Mechanochemical organic synthesis; Diastereoselective synthesis; ASYMMETRIC ALDOL REACTION; SYNTHASE KINASE 3; (S)-PROLINE-CONTAINING DIPEPTIDES; CYCLIZATION; VALMERINS; ORGANOCATALYSTS; MAGALLANESINE; GENERATION; INHIBITORS; CHEMISTRY;

D O I：

10.1016/j.tet.2019.130594

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly diastereoselective synthesis, crystallographic analysis, and full characterization of several novel heterocycle-fused isoindolones is described. The synthetic strategy involves a cascade Michael/aldol-like cyclization reaction between N-substituted phthalimides rac-1 or 2 and several alpha,beta-unsaturated electrophiles to afford the tricyclic systems pyrrolo[2,1-a]isoindolone and tetrahydropyrido[2,1-a] isoindolone. This synthetic strategy offers a convenient alternative to existing procedures for the preparation of isoindolone derivatives fused to five- and six-membered rings. X-ray crystallographic analysis allowed the determination of relative configurations and revealed that the synthesized compounds exhibit significant structural distortion, especially in the five membered rings. Relevantly, the diastereomeric distribution of products depends substantially on whether the cascade reaction is carried out under solution vis-a-vis solvent-free conditions. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页数：11

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