Next Article in Journal
3-(1-Phenyl-1H-pyrazol-4-yl)-1,2-benzisoxazole 2-oxide
Previous Article in Journal
7-Hydroxy-8-acetylcoumarin N-1-(Carboxymethyl)pyridinium Chloride Hydrazone
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2008
Issue 2
10.3390/M572
molbank-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

9-Methyl-2H-chromeno[8,7-d]isoxazol-2-one N-oxide

by
Antigoni Kotali
1,*,
Ioannis S. Lafazanis
1 and
Philip A. Harris
2
1
Laboratory of Organic Chemistry, Department of Chemical Engineering, College of Engineering, University of Thessaloniki, Thessaloniki 54124, Greece
2
GlaxoSmithKline, 1250 South Collegeville Road, P.O.Box 5089, Collegeville, PA 19426-0989, USA
*
Author to whom correspondence should be addressed.
Molbank 2008, 2008(2), M572; https://doi.org/10.3390/M572
Submission received: 24 April 2007 / Revised: 8 August 2008 / Accepted: 18 August 2008 / Published: 24 August 2008
Versions Notes

As part of a research programme targeting novel molecules derived from nitrogen derivatives of o-hydroxyaryl ketones [1] we synthesised 7-hydroxy-8-acetylcoumarin oxime and we subsequently oxidized it with lead tetraacetate (LTA) as well as with diacetoxy iodobenzene (DIB). The reactions led to the formation of the oxidative cyclisation product, 9-methyl-2H-chromeno[8,7-d]isoxazol-2-one N-oxide , in good yields. It is well known that isoxazole ring possesses interesting biological activity especially as acetyl cholesterinase inhibitor [2] and as antimicrobial agent [3].
Molbank 2008 m572 i001
7-Hydroxy-8-acetylcoumarin oxime was prepared according to the literature method [4] whereas commercially available lead tetraacetate as well as diacetoxy iodobenzene were supplied by Aldrich.

Method A

1.37 g (3.09 mmol) of LTA are added to a suspension of 0.5 g (2.30 mmol) of 7-hydroxy-8-acetylcoumarin oxime in 20 ml THF in an ice-bath. The mixture was then stirred magnetically at 0-4 οC for 2 hrs. Filtration of the precipitate, which was formed, gave a solid which was recrystillised from petroleum ether to afford (0.33 g, 67 %) of the desired as white crystals. The product was identified by its 1H NMR, 13C NMR and MS and elemental analysis.

Method B

0.75 g (2.33 mmol) of DIB are added to a suspension of 0.5 g (2.30 mmol) of 7-hydroxy-8-acetylcoumarin oxime in 20 ml CH2Cl2 in an ice-bath. The mixture was then stirred magnetically at r.t. for 24 hrs. Evaporation of the solvent gave an oil which was then subjected to column chromatography (silica gel 70-230 mesh). Elution with a mixture of petroleum ether / ethylacetate 1:1 afforded (0.32 g, 65 %) the desired as white crystals. The product was identified by its 1H NMR, 13C NMR and MS and elemental analysis.
M.p. 208.5-209.5 °C.
1H NMR (400 MHz, DMSO-d6): 2.47 (s, 3H), 6.47-6.50 (d, 1H, J=9.7),7.32-7.34 (d, 1H, J=8.6), 7.83-7.85 (d, 1H, J=8.6), 8-11-8.13 (d, 1H, J=9.7).
13C NMR (100 MHz, DMSO-d6): 11.2, 104.7, 109.7, 115.0, 115.2, 128.9, 129.5, 139.7, 145.5, 151.8, 159.5.
MS m/z (ES+): 240 [M+Na]+, 217 [M]+, 202, 201, 187.
Anal. Calc. for C11H7NO4: C 60.83, H 3.25, N 6.45; found: C 60.73, H 3.22, N, 6.39.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Kotali, A.; Harris, P. A. Org. Prep. Proc. Int. 1994, 26(2), 155.
  2. Rangappa, S. Biorganic and Med. Chem. 1994, 37, 2721.
  3. Priya, B.S.; Bassappa, S.; Nanjunda, S.; Rangappa, S. Biorganic and Med. Chem. 2005, 13, 2623.
  4. Thakkar, K.; Cushman, K. Tetrahedron Lett. 1994, 35(35), 6441.

Share and Cite

MDPI and ACS Style

Kotali, A.; Lafazanis, I.S.; Harris, P.A. 9-Methyl-2H-chromeno[8,7-d]isoxazol-2-one N-oxide. Molbank 2008, 2008, M572. https://doi.org/10.3390/M572

AMA Style

Kotali A, Lafazanis IS, Harris PA. 9-Methyl-2H-chromeno[8,7-d]isoxazol-2-one N-oxide. Molbank. 2008; 2008(2):M572. https://doi.org/10.3390/M572

Chicago/Turabian Style

Kotali, Antigoni, Ioannis S. Lafazanis, and Philip A. Harris. 2008. "9-Methyl-2H-chromeno[8,7-d]isoxazol-2-one N-oxide" Molbank 2008, no. 2: M572. https://doi.org/10.3390/M572

APA Style

Kotali, A., Lafazanis, I. S., & Harris, P. A. (2008). 9-Methyl-2H-chromeno[8,7-d]isoxazol-2-one N-oxide. Molbank, 2008(2), M572. https://doi.org/10.3390/M572

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop