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One‐Pot stereoselective synthesis of trans ‐4,5‐dialkoxy‐1,3‐bis (2‐pyrimidinyl)imidazolidines through a three‐component reaction
Author(s) -
Ghandi Mehdi,
Salimi Farshid,
Olyaei Abolfazl
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430342
Subject(s) - chemistry , imidazolidine , glyoxal , formic acid , acetonitrile , stereoselectivity , formaldehyde , catalysis , medicinal chemistry , alcohol , stoichiometry , organic chemistry , polymer chemistry
toichiometric reaction of 2‐aminopyrimidine with formaldehyde in the presence of formic acid catalyst in water gave N,N ′‐bis(2‐pyrimidinyl)methanediamine ( 5 ). Subsequent cyclocondensation of 5 with glyoxal in alcohol (MeOH, EtOH, PrOH and i ‐PrOH) under reflux conditions led to the formation of the corresponding 4,5‐dialkoxy‐1,3‐bis(2‐pyrimidinyl)imidazolidines ( 6a‐d ). 4,5‐Dihydroxy‐1,3‐bis(2‐pyrimidinyl) imidazolidine ( 6e ) was obtained when the reaction was carried out in acetonitrile. Based on 1 H NMR analysis, it was found that the trans ‐dialkoxyimidazolidines ( 6 ) were selectively obtained in these cyclocondensation reactions.