On-column N-dearylation of 2-azetidinones by silica-supported ceric ammonium nitrate

被引：23

作者：

Zarei, Maaroof ^{[2
]}

Jarrahpour, Aliasghar ^{[1
]}

Ebrahimi, Edris ^{[1
]}

Aye, Malihe ^{[1
]}

Badrabady, Seid Ali Torabi ^{[1
]}

机构：

[1] Shiraz Univ, Dept Chem, Coll Sci, Shiraz 71454, Iran

[2] Hormozgan Univ, Dept Chem, Coll Sci, Bandar Abbas 71961, Iran

来源：

TETRAHEDRON | 2012年 / 68卷 / 27-28期

关键词：

On-column reaction; N-Dearylation; N-Unsubstituted; 2-azetidinone; beta-Lactam; Ceric ammonium nitrate; Silica-supported; MONOCYCLIC BETA-LACTAMS; SOLID-SOLID PHASE; STEREOSELECTIVE-SYNTHESIS; BUILDING-BLOCKS; ALPHA-AMINO; OXIDATIVE DEMETHYLATION; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; VILSMEIER REAGENT; CONCISE SYNTHESIS;

D O I：

10.1016/j.tet.2012.04.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modified traditional preparative chromatographic column can be used to achieve quantitative N-dearylation of N-(alkoxyphenyl), N-(alkoxynaphthyl), and N-(alkoxybenzyl)-2-azetidinones under mild conditions. Starting materials are charged on top of the column and the pure N-unsubstituted 2-azetidinones leave the column minutes later without need for other purifications. The yields are good-to-excellent and the reaction condition is mild, easy, efficient, and cheap. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5505 / 5512

页数：8

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