Reactions of trimethylsilyl isocyanate and isothiocyanate with 3-(dialkylamino)-2H-azirines. A facile synthesis of 1-unsubstituted 4-(dialkylamino) imidazolin-2-ones …

I Handke, E Schaumann…

Index: Handke, Isabel; Schaumann, Ernst Journal of Organic Chemistry, 1988 , vol. 53, # 22 p. 5298 - 5300

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Citation Number: 9

Abstract

The reaction of azirines ta, b, d, e with trimethylsilyl isocyanate (4) or isothiocyanate (5) gives imidazolinones 6a, b, e and thiones 7a, b, d, e, respectively. However, in an alternate reaction course, azirine 3c leads to amidinium salts 9. The potential of the products for chemical modification is shown by hydrolysis of 7a to give 12 and by the oxidative desulfurization of 7a, d to furnish 6a, d.