From Solution-Phase to ‘On-Column’ N-Dearylation of β-Lactams by Silica-Supported Ceric Ammonium Nitrate (CAN-SiO2)

Aliasghar Jarrahpour; Maaroof Zarei

doi:10.1055/s-2008-1032051

LETTER

From Solution-Phase to ‘On-Column’ N-Dearylation of β-Lactams by Silica-Supported Ceric Ammonium Nitrate (CAN-SiO₂)

Aliasghar Jarrahpour*, Maaroof Zarei
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2280926; e-Mail: jarrah@chem.susc.ac.ir; e-Mail: aliasghar6683@yahoo.com;

Abstract

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Abstract

It has been shown that N-(4-methoxy or 4-ethoxyphenyl) groups can be oxidatively removed by silica gel supported ceric ammonium nitrate (CAN-SiO₂) under mild conditions in solution and on column. The yields in these two methods were good to excellent and purification of products is simpler than the general method by CAN. Especially the ‘on-column’ reaction is mild, easy, efficient, and cheap. The lower mobility of CAN-SiO₂ makes it safer to handle.

Key words

on-column reaction - N-dearylation - N-unsubstituted 2-azetidinone - β-lactam - ceric ammonium nitrate - silica supported

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