Heterocyclic Nonionic X-ray Contrast Agents. III. The Synthesis of 5-[4-(Hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide Derivatives

Autor:	R. S. Ranganathan, K. M. R. Pillai, L. Duncan, G. Diamantidis
Rok vydání:	1994
Předmět:	Atropisomer Intramolecular reaction medicine.drug_class Organic Chemistry Glycidol Regioselectivity Carboxamide Medicinal chemistry chemistry.chemical_compound chemistry Intramolecular force medicine Moiety Hydroxymethyl
Zdroj:	The Journal of Organic Chemistry. 59:1344-1350
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00085a023
Popis:	The syntheses of 2,4,6-triiodo-1,3-benzenedicarboxamide analogs, (12c), (12e), and (17c), of interest as X-ray diagnostic agents and in which the 5 position is linked to the N atom of a 4-(hydroxymethyl)-oxazoli- din-2-one moiety, are described. The heterocycle was built from suitably protected 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid derivati- ves by a three-step procedure consisting of (1) phosgene treatment to obtain the corresponding isocyanates, (2) phenylmercuric chloride-cata- lyzed addition of glycidol (10) resulting in glycidyl carbamates, and (3) pyridine-catalyzed intramolecular N-alkylation, followed by depro- tection, to obtain the oxazolidin-2-ones. The intramolecular N-alkyla- tion reaction was highly regioselective and was not appreciably accom- panied by O-alkylation products under the experimental conditions emp- loyed. These highlt congested benzenoid compounds exhibited intersting NMR spectral features due to atropisomerism arising from hindrance to free rotation about the three single bonds that link the aromatic moiety to the N-containing functionalities
Databáze:	OpenAIRE
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