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

Mrkvička Vladimír | Zendy; Lyčka Antonín | Zendy; Vícha Robert | Zendy; Klásek Antonín | Zendy

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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.

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