Schmidt reaction of some constrained aromatic acids, and related topics

EH Ruediger, SS Gandhi, MS Gibson…

Index: Ruediger, Edward H.; Gandhi, Sham S.; Gibson, Martin S.; Farcasiu, Dan; Uncuta, Cornelia Canadian Journal of Chemistry, 1986 , vol. 64, p. 577 - 579

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Citation Number: 9

Abstract

Schmidt reaction of phthalic acid in 90-98% sulfuric acid gives anthranilic acid and anthranilazide (major products) by a process considered to involve 3, 1-benzoxazin-2, 4 (1 H)-dione as intermediate. Benzimidazol-2-one is produced in this reaction by a secondary process from anthranilazide; it is also produced by photolysis of anthranilazide. Under Schmidt reaction conditions, 1, 2, 3-benzotriazin-4 (3 H)-one gives o-azidobenzamide. ...