Issue 7, 2005
From the journal:

New Journal of Chemistry

A simple and efficient synthesis of 2-imidazolin-2-ones

Sergeja Bombek,a   Franc Požgan,a   Marijan Kočevara  and  Slovenko Polanc*a  

* Corresponding authors

a Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, Ljubljana, Slovenia
E-mail: slovenko.polanc@fkkt.uni-lj.si
Fax: +386-1-24-19-271
Tel: +386-1-24-19-236

Abstract

We report on the reactions of diazenes 1 and 2 with 1,3-dicarbonyl compounds. The first step involves a regioselective attack of the diazene on the active methylene group, giving the Michael adducts 3 or 4, and can be performed either in the presence of sodium acetate or DBN (1,5-diazabicyclo[4.3.0]non-5-ene). The Michael adducts underwent ring-closure leading to 2-imidazolidinones 5 or 6 which were isolated in some cases. We found that 5 or 6 easily eliminated water in the presence of an acid to give imidazolin-2-ones 7 or 8 as the final products. The rate-determining step of this last mentioned process depends on the stereochemistry at C4 and C5 of the initial 2-imidazolidinone. A one-pot procedure to produce 7 or 8 directly from the diazene and the appropriate dicarbonyl partner is also described.

Graphical abstract: A simple and efficient synthesis of 2-imidazolin-2-ones

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Article information

DOI
https://doi.org/10.1039/B502719E
Article type
Paper
Submitted
22 Feb 2005
Accepted
26 Apr 2005
First published
09 Jun 2005

New J. Chem., 2005,29, 948-954

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A simple and efficient synthesis of 2-imidazolin-2-ones

S. Bombek, F. Požgan, M. Kočevar and S. Polanc, New J. Chem., 2005, 29, 948 DOI: 10.1039/B502719E

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