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synthesis of symmetrical and non-symmetrical diimines from dimedone从双甲酮合成的对称和不对称二亚胺
Molecules 2009, 14, 2278-2285; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Synthesis of Symmetrical and Non-symmetrical Diimines from
Dimedone
Bahjat A. Saeed * and Ibrahim A. Musad
University of Basrah, College of Education, Chemistry Department, Basrah, Iraq
* Author to whom correspondence should be addressed; E-mail: bas_chem_dep@
Received: 7 May 2009; in revised form: 21 May 2009 / Accepted: 9 June 2009 /
Published: 24 June 2009
Abstract: Symmetrical and non-symmetrical diimines derived from dimedone were
synthesized by the reaction of their corresponding enaminothiones with primary amines.
The synthesized compounds were characterized using micro analytical data and NMR
spectroscopy. Theoretical calculations by B3LYP/6-31G(d,p) level of theory show that the
enolic form is the most stable within the possible tautomeric forms of the compounds.
Keywords: dimedone; diimines; enaminothiones; B3LYP/6-31G(d,p)
Introduction
Diimines of β-diketones have received significantly increasing attention which stems from the
scope for variation of the substituents on the nitrogen atoms [1]. In addition, they have been used as
precursors to some heterocyclic compounds such as imidazolines, pyrimidines and carbapenem
intermediates [2,3]. There are two synthetic procedures for the conversion of β-diketone into a β-
diketimine [1]. The first is to convert the diketone to the dioxyalkanone, which is t
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