- Schmidt reaction of some constrained aromatic acids, and related topics
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Schmidt reaction of phthalic acid in 90-98percent sulfuric acid gives anthranilic acid and anthranilazide (major products) by a process considered to involve 3,1-benzoxazin-2,4(1H)-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(3H)-one gives o-azidobenzamide.Under similar conditions, the lactol of 4-formyl-5-phenanthroic acid gives 1-azapyren-2(1H)-one and phenanthrene-4,5-dicarboximide, while phenanthrene-4,5-dicarboxylic acid gives 1-azapyren-2(1H)-one.Diphenic acid yields phenanthridone and 2,2'-diaminobiphenyl in proportions dependent on the sulfuric acid concentration.
- Ruediger, Edward H.,Gandhi, Sham S.,Gibson, Martin S.,Farcasiu, Dan,Uncuta, Cornelia
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p. 577 - 579
(2007/10/02)
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