L.I.L. Cabral et al. / Tetrahedron 69 (2013) 810e815
815
(1H, m), 1.72 (3H, d, J¼7.1 Hz) (see Figs. S2, S4, Supplementary data,
References and notes
for 1NMR and mass spectra).
1. , Otten, M.; von Deyn, W.; Engel, S.; Hill, R.; Kardorff, U.; Vossen, M.; Plath, P.
Isoxazole-4-yl-benzoyl derivatives and their use as herbicides, Patent
WO9719076, Internationale Anmeldung Veroffentlicht nach dem Vertrag uber
die Internationale Zusammenargeit auf dem Gebiet des Patentwesens.
Weltorgani-sationfur Geistiges Eigentum, 1997.
2. Wepplo, P. J.; Rampulla, R. A.; Heffernan, G. D.; Cosette, M. V.; Diehl, R. E.;
Fiordeliso, J. J.; Haley, G. J.; Guaciaro, M. A. Herbicidal 3-heterocyclic substituted
benzisothiazole and benzisoxazole compounds, Patent WO0179203, Interna-
tionale Anmeldung Veroffentlicht nach dem Vertrag uber die Internationale
Zusammenargeit auf dem Gebiet des Patentwesens. Weltorganisationfur
Geistiges Eigentum, 2004.
3. Gravestock, M. B. Bicyclic heterocyclic substituted phenyl oxazolidinone anti-
bacterials, and related compositions and methods, Patent WO/1999/10342,
Internationale Anmeldung Veroffentlicht nach dem Vertrag uber die Inter-
nationale Zusammenargeit auf dem Gebiet des Patentwesens. Weltorganisa-
tionfur Geistiges Eigentum, 1999.
4. Eacho, P. I.; Foxworthy-Mason, P. S.; Lin, H. -S.; Lopez, J. E.; Mosior, M.;
Richett, M. E. Benzisothiazol-3-one-carboxylic acid amides as phospholi-
pase inhibitors, Patent WO/2004/094394. Internationale Anmeldung
Veroffentlicht nach dem Vertrag uber die Internationale Zusammenargeit
auf dem Gebiet des Patentwesens. Weltorganisationfur Geistiges Eigentum,
2004.
4.2. Infrared spectroscopy
The infrared spectra, in the 500e4000 cmꢁ1 range, were
recorded for the compound diluted in a KBr pellet, using a Thermo
Nicolet IR300 FTIR spectrometer, resolution 1 cmꢁ1, or a Bomem
MB104 FT-spectrometer, with 4 cmꢁ1 resolution, and either a SPE-
CAC variable temperature infrared cell with an iron/constantan
(copperenickel) J-type thermocouple, connected to a digital con-
troller (Shinho, MCD 530; accuracy ca. ꢀ2 ꢃC), or a modified DTA
cell Mettler-Toledo FP90 thermosystem with a Pt100 precision
sensor (accuracy ꢀ0.1 ꢃC) (Figs. 1 and 2). The sample compartment
of the spectrometer was purged during all experiments by means of
a constant flux of dry nitrogen, to avoid contamination from ab-
sorptions due to atmospheric water and CO2.
4.3. Differential scanning calorimetry (DSC) and polarized
light thermo-microscopy (PLTM)
5. Hlasta, D. J.; Bell, M. R.; Court, J. J.; Cundy, K. C.; Desai, R. C.; Ferguson, E. W.;
Gordon, R. J.; Kumar, V.; Maycock, A. L.; Subramanyam, C. Bioorg. Med. Chem.
Lett. 1995, 5, 331.
6. Subramanyam, C.; Bell, M. R.; Ferguson, E.; Gordon, R. G.; Dunlap, R. P.; Franke,
C.; Mura, A. J. Bioorg. Med. Chem. Lett. 1995, 5, 319.
7. Wang, L. H.; Yang, X. Y.; Zhang, X.; Mihalic, K.; Fan, Y. X.; Xiao, W.;
Zack Howard, O. M.; Appella, E.; Maynard, A. T.; Farrar, W. L. Nat. Med. 2004,
10, 40.
DSC experiments were performed using a Perkin Elmer DSC7
calorimeter, with an intracooler cooling unit at ꢁ10 ꢃC (ethyl-
eneglycol/water 1:1 v/v cooling mixture). The samples were her-
metically sealed in aluminum pans and as reference an empty pan
was used. A 20 mL minꢁ1 nitrogen purge was employed. Temper-
ature and enthalpy calibration were performed as in previous au-
thors’ work32 with high-grade standards, namely, biphenyl (CRM
LGC 2610, Tfus¼68.93ꢀ0.03 ꢃC) and indium (Perkin Elmer,
x¼99.99%, Tfus¼156.60 ꢃC). Enthalpy calibration was performed
with indium (DfusH¼3286ꢀ13 J molꢁ1). DSC curves were analyzed
with Pyris software version 3.5.
8. Sharmeen, L.; McQuade, T.; Heldsinger, A.; Gogliotti, R.; Domagala, J.; Gracheck,
S. Antiviral Res. 2001, 49, 101.
9. Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D. Chem. Rev. 1985, 85, 129.
ꢀ
~
10. Araujo, N. C. P.; Brigas, A. F.; Cristiano, M. L. S.; Frija, L. M. T.; Guimaraes, E. M. O.;
Loureiro, R. M. S. J. Mol. Catal. A: Chem. 2004, 215, 113.
~
11. Frija, L. M. T.; Cristiano, M. L. S.; Guimaraes, E. M. O.; Martins, N. C.; Loureiro, R.
M. S.; Bikley, J. J. Mol. Catal. A: Chem. 2005, 242, 241.
12. Barkley, J. V.; Cristiano, M. L. S.; Johnstone, R. A. W.; Loureiro, R. M. S. Acta
Crystallogr., Sect. C: Cryst. Struct. Commun. 1997, 53, 383.
13. Cristiano, M. L. S.; Brigas, A. F.; Johnstone, R. A. W.; Loureiro, R. M. S.; Pena, P. C.
The polarized light thermomicroscopy was performed in
a Linkam DSC600 system attached to a DMRB Leica microscope fitted
with polarized light facilities, connected to a Sony CCD-IRIS/RGB
video camera. A Linkam system software with Real Time Video
Measurement was used for image analysis. A small amount of the
sample to be studied was placed in a 7 mm glass crucible used as
a cell, which was covered with a glass lid. Thermal cycles were per-
formed at 10 ꢃC minꢁ1, and the images obtained by combined use of
polarized light and wave compensators at 200ꢂ magnification. Bi-
phenyl and benzoic acid were used to confirm temperature accuracy.
A. J. Chem. Res., Synop. 1999, 704.
14. Araujo, N. C. P.; Barroca, P. M. M.; Bickley, J. F.; Brigas, A. F.; Cristiano, M. L. S.;
ꢀ
Johnstone, R. A. W.; Loureiro, R. M. S.; Pena, P. C. A. J. Chem. Soc., Perkin Trans. 1
2002, 1213.
ꢀ
ꢀ
15. Gomez-Zavaglia, A.; Kaczor, A.; Almeida, R.; Cristiano, M. L. S.; Eusebio, M. E. S.;
Maria, T. M. R.; Mobili, P.; Fausto, R. J. Phys. Chem. A 2009, 113, 3517.
ꢀ
ꢀ
16. Almeida, R.; Gomez-Zavaglia, A.; Kaczor, A.; Cristiano, M. L. S.; Eusebio, M. E. S.;
Maria, T. M. R.; Fausto, R. Tetrahedron 2008, 64, 3296.
17. Kaczor, A.; Proniewicz, L.; Almeida, R.; Gomez-Zavaglia, A.; Cristiano, M. L. S.;
Matos Beja, A. M.; Ramos Silva, M.; Fausto, R. J. Mol. Struct. 2008,
892, 343.
18. Cristiano, M. L. S.; Johnstone, R. A. W.; Price, P. J. J. Chem. Soc., Perkin Trans. 1
ꢀ
1996, 1453.
19. Cristiano, M. L. S.; Johnstone, R. A. W. J. Chem. Soc., Perkin Trans. 2 1997, 489.
20. Cristiano, M. L. S.; Johnstone, R. A. W. J. Chem. Res. 1997, 164.
21. Frija, L. M. T.; Reva, I.; Ismael, A.; Coelho, D. V.; Fausto, R.; Cristiano, M. L. S. Org.
Biomol. Chem. 2011, 9, 6040.
22. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Chemie
GmbH: Weinheim, 1970.
23. Ito, H.; Tagushi, T. Chem. Soc. Rev. 1999, 28, 43.
24. Zipse, H. H. J. Chem. Soc., Perkin Trans. 2 1996, 1797.
25. Birney, D. M.; Xu, X.; Ham, S. Angew. Chem., Int. Ed. 1999, 38, 189.
26. Pauling, L. J. Am. Chem. Soc. 1947, 69, 542.
Acknowledgements
~
The research was supported by the Portuguese Fundac¸ ao para
ˇ
a Ciencia e a Tecnologia, COMPETE and FEDER (Project PTDC/QUI-
QUI/1118779/2009). Authors thanks the Nuclear Magnetic Reso-
nance
Laboratory of
the Coimbra
Chemistry
Centre
grant REEQ/481/QUI/2006 from FCT, POCI-2010 and FEDER, Portugal.
27. Handbook of Chemistry & Physics; Lide, D. R., Ed.; CRC: Boca Raton, 1993e94;
pp 9-1e9-41.
€
28. Burgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153.
ꢀ
29. Gomez-Zavaglia, A.; Kaczor, A.; Almeida, R.; Cristiano, M. L. S.; Fausto, R. J. Phys.
Supplementary data
Chem. A 2008, 112, 1762.
ꢀ
30. Gomez-Zavaglia, A.; Kaczor, A.; Coelho, D.; Cristiano, M. L. S.; Fausto, R. J. Mol.
1NMR and mass spectra for CBID and CBIOD (Figs. S1eS4) and
proposed assignments for the full set of observed bands in IR
spectra of both compounds (Tables S5, S6). Supplementary data
Struct. 2009, 919, 271.
31. Coates, R. M.; Rogers, B. D.; Hobbs, S. J.; Peck, D. R.; Curran, D. P. J. Am. Chem. Soc.
1987, 109, 1160.
32. Burrows, C. J.; Carpenter, B. K. J. Am. Chem. Soc. 1981, 103, 6983.
33. Maria, T. M. R.; Castro, R. A. E.; Bebiano, S. S.; Ramos Silva, M.; Matos Beja, A.;
ꢀ
Canotilho, J.; Eusebio, M. E. S. Cryst. Growth Des. 2010, 10, 1194.