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Molecular Rearrangement of 9b‐Hydroxy‐1 H ‐imidazo[4,5‐ c ]quinoline‐2,4‐diones – A Convenient Pathway to Spiro‐Linked Imidazolidine–Oxindole Derivatives
Author(s) -
Klásek Antonín,
Lyčka Antonín,
Mikšík Ivan,
Růžička Aleš
Publication year - 2009
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.200800338
Subject(s) - chemistry , quinoline , imidazolidine , aryl , alkyl , medicinal chemistry , stereochemistry , organic chemistry
The 1‐substituted 3‐alkyl/aryl‐3‐aminoquinoline‐2,4(1 H ,3 H )‐diones 1 react with alkyl/aryl isocyanates to give novel 3‐alkyl/aryl‐3‐ureidoquinoline‐2,4(1 H ,3 H )‐diones (= N ‐(3‐alkyl/aryl‐1,2,3,4‐tetrahydro‐2,4‐dioxoquinolin‐3‐yl)ureas) 2 and/or 3a‐alkyl/aryl‐3,3a,5,9b‐tetrahydro‐9b‐hydroxy‐1 H ‐imidazo[4,5‐ c ]quinoline‐2,4‐diones 3 in high yields. Compounds 2 and 3 rearrange by boiling in AcOH or concentrated HCl solution to give three different types of spiro[imidazolidine‐4,3′‐[3 H ]indole]‐2,2′(1′ H )‐diones, i.e. , 10, 11 , and 12 , depending on the kind of substituents at C(3) and C(3a), respectively. All compounds were characterized by 1 H‐ and 13 C‐NMR and IR spectroscopy as well as by atmospheric‐pressure chemical‐ionization (APCI) mass spectra. The structures of compounds 11c and 12Al were investigated by single‐crystal X‐ray diffraction analysis.