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Reaction of 3‐Hydroxyquinoline‐2,4‐diones with Isocyanates and Thermally Induced Transformation of the Reaction Products
Author(s) -
Mrkvička Vladimír,
Lyčka Antonín,
Vícha Robert,
Klásek Antonín
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000128
Subject(s) - chemistry , quinoline , 8 hydroxyquinoline , pyridine , mass spectrometry , aryl , medicinal chemistry , nuclear magnetic resonance spectroscopy , alkyl , organic chemistry , isocyanate , boiling , chromatography , polyurethane
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.