Reactions of Isatoic Anhydride with Carbanions

Sulfonylmethylene compounds such as methyl sulfonylacetate (220 R2 = Me, R3 = OEt) or phenyl phenacyl sulfone (220 R2 = R3 = Ph) give with N-substituted IA the corresponding 4-hydroxy-3-sulfonyl-2-quinolones 

IA and hydrogen sulfide react to form the isatoates 255 and their decar-boxylated products 256.110,111,286-288 Oxidation of 256 with iodine288 or H202286,287 leads to benzoisothiazolinones (259). Treatment of 256 with isoamyl nitrite or HNOz produces benzothiadiazinone (258),110,111 which 

Hariri, Ph.D. Thesis, University of Graz, Austria (1976) T. Kappe, M. Hariri, and E. Pongratz, Monatsh. Chem. (in press). 

Reaction of IA with aziridine in the presence of hydrogen sulfide leads to the unstable intermediate 277, which produced the thiazoloquinazoline 278 with ethyl chloroformate (Eq. 24).293 Ring opening of IA to the anthranilate 

279 followed by a Grignard reaction to the alcohol 280 gives the cinnoline 282by subsequent dehydratation and diazotization (Eq. 25).294 N-Methyl-IA 

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