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Synthesis, Properties and Structure of 1‐Acetyl‐6‐(4‐chlorobenzylidene)‐2,3,5,6‐tetrahydroimidazo[2,1‐ b ]imidazole‐3,5‐dione
Author(s) -
KiećKoowicz Katarzyna,
KarolakWojciechowska Janina
Publication year - 1995
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19953280205
Subject(s) - chemistry , imidazole , stereochemistry , reactivity (psychology) , crystal structure , nucleophile , computational chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Abstract Cyclization of N ‐[5‐(4‐chlorobenzylidene]‐4‐oxo‐2‐imidazolidinyl]glycine ( 4 ) in acetic acid anhydride yielded 1‐acetyl‐6‐(4‐chlorobenzylidene)‐2,3,5,6‐tetrahydroimidazo[2,1‐ b ]imidazole‐3,5‐dione ( 5 ). The structure of 5 was ascribed on basis of its MS, 1 H‐ and 13 C‐NMR properties. The crystal structure of 5 was solved by X‐ray analysis. On the basis of semiempirical quantum chemistry calculations (PM3 method) the thermodynamic stability of theoretically possible cyclization products was determined. These data allow to predict the direction of cyclization. The stability and the reactivity of 5 toward nucleophilic attack were examined.