An unprecedented rearrangement of salicylanilide derivatives: imidazolinone intermediate formation

The ORTEP view of 2-(5-chloro-2-hydroxyphenyl)-3-(3-chlorophenyl)-5-isopropyl-3,5-dihydro-4 H-imidazol-4-one, a dehydrated form of reaction intermediate. The preparation of new prodrug forms of anti-tuberculosis active salicylanilide esters with amino acids led to an unexpected rearrangement. The is...

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Published in:Tetrahedron letters 2010-01, Vol.51 (1), p.23-26
Main Authors: Vinsova, Jarmila, Imramovsky, Ales, Kratky, Martin, Ferriz, Juana Monreal, Palat, Karel, Lycka, Antonin, Ruzicka, Ales
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description The ORTEP view of 2-(5-chloro-2-hydroxyphenyl)-3-(3-chlorophenyl)-5-isopropyl-3,5-dihydro-4 H-imidazol-4-one, a dehydrated form of reaction intermediate. The preparation of new prodrug forms of anti-tuberculosis active salicylanilide esters with amino acids led to an unexpected rearrangement. The isolation and the structure determination of 2-(5-chloro-2-hydroxyphenyl)-3-(3-chlorophenyl)-5-substituted-3,5-dihydro-4 H-imidazol-4-ones unambiguously confirm one of the two proposed reaction mechanisms.
doi_str_mv 10.1016/j.tetlet.2009.10.084
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title An unprecedented rearrangement of salicylanilide derivatives: imidazolinone intermediate formation
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