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Molecular Rearrangement of 9b-Hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones – A Convenient Pathway to Spiro-Linked Imidazolidine–Oxindole Derivatives

✍ Scribed by Antonín Klásek; Antonín Lyčka; Ivan Mikšík; Aleš Růžička

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
323 KB
Volume
92
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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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.

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