The Schmidt reaction of anthraquinones

CA Flemming, SS Gandhi, MS Gibson…

Index: Flemming, Cecily A.; Gandhi, Sham S.; Gibson, Martin S.; Ruediger, Edward H. Canadian Journal of Chemistry, 1982 , vol. 60, p. 624 - 628

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Citation Number: 4

Abstract

Schmidt reaction (sodium azide/sulfuric acid) of 1, 5-and of 1, 8-dichloroanthraquinones gives, in each case, both of the theoretically possible lactams (2, 3, 5, 6-dibenzoazepin-4, 7- diones). Two of the four theoretically possible lactams have been identified from Schmidt reaction of 1-and 2-chloroanthraquinones respectively. Methods used include:(a) preferential hydrolysis of one lactam and identification of the isomeric ...