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Reaction of 3-Hydroxyquinoline-2,4-diones with Isocyanates and Thermally Induced Transformation of the Reaction Products

✍ Scribed by Vladimír Mrkvička; Antonín Lyčka; Robert Vícha; Antonín Klásek

Publisher: John Wiley and Sons
Year: 2011
Tongue: German
Weight: 195 KB
Volume: 94
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.201000128

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✦ Synopsis

Abstract

3‐Hydroxyquinoline‐2,4‐diones 1 react with isocyanates to give novel 1,2,3,4‐tetrahydro‐2,4‐dioxoquinolin‐3‐yl (alkyl/aryl)carbamates 2 and/or 1,9b‐dihydro‐9b‐hydroxyoxazolo[5,4‐c]quinoline‐2,4(3a__H__,5__H__)‐diones 3. Both of these compounds are converted, by boiling in cyclohexylbenzene solution in the presence of Ph~3~P or 4‐(dimethylamino)pyridine, to give 3‐(acyloxy)‐1,3‐dihydro‐2__H__‐indol‐2‐ones 8. All compounds were characterized by IR, and ^1^H‐ and ^13^C‐NMR spectroscopy, as well as by EI mass spectrometry.

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