One‐Pot stereoselective synthesis of  trans ‐4,5‐dialkoxy‐1,3‐bis (2‐pyrimidinyl)imidazolidines through a three‐component reaction | Zendy

Ghandi Mehdi | Zendy; Salimi Farshid | Zendy; Olyaei Abolfazl | Zendy

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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.

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