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Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1383-1389
Published online, 1st November, 2011
DOI: 10.3987/COM-11-S(P)99
The Synthesis and Antimicrobial Evaluation of Some Spiro-Phthalidyl Benzoxazinones

Caterina Ferraro, István Lengyel, and Ralph Stephani*

*Department of Chemistry, St. John's University, 8000 Utopia Parkway, Jamaica, New York 11439, U.S.A.


Five N-substituted spiro-phthalidyl benzoxazinones (5a-e) were prepared from anthranilic acid (1) and the appropriate alkyl or aryl halides (2), followed by condensation of the N-substituted anthranilic acids (3) with symmetrical phthaloyl dichloride (4). These compounds were then evaluated for antimicrobial activity against: E. coli, S. aureus, B. subtilis, P. aeruginosa, S. cerevisiae, and A. nidulans. Compound 5a was active against all the microbes tested, especially the A. nidulans. Compound 5c was active against all the bacteria, except the fungus A. nidulans. The N-benzyl (5b) and N-phenyl (5d) derivatives were not active at all. The N-4-fluorophenyl analog 5e showed activity against S. aureus and B. subtilis.