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Chemical behaviour of N ‐(2‐hydroxybenzyl)anthranilic acids in the presence of acyclic anhydrides
Author(s) -
Aversa M. C.,
Bonaccorsi P.,
Giannetto P.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260528
Subject(s) - chemistry , heteronuclear molecule , anthranilic acid , acetic anhydride , mass spectrum , organic chemistry , isobutyric acid , carbon 13 nmr , mass spectrometry , nuclear magnetic resonance spectroscopy , medicinal chemistry , stereochemistry , chromatography , catalysis
The synthesis of 11‐acyl‐11,12‐dihydrodibenz[ bf ][1,5]oxazocin‐6‐ones 9‐13 is reported by reaction of N ‐(2‐hydroxybenzyl)anthranilic acids 1 with acetic, isobutyric, 2‐ethylbutyric anhydrides. The structures of the obtained 6,8,6 products are proved with the use of ir, mass spectrometry, 1 H and 13 C nmr spectra, homo‐and heteronuclear two‐dimensional nmr experiments. The formation of 9‐13 is discussed in relation to the obtainment of 12 H ‐quino[2,1‐ b ][1,3]benzoxazin‐5‐ones 2‐8 and 6a,12‐dihydro[3,1]benzoxazino[2,1‐ b ][1,3]‐benzoxazin‐5‐ones 14‐19 from the same starting products 1 with suitable anhydrides under controlled reaction conditions.