3
8.
9.
Sherrington, D. C.; Kybett, A. P., Eds. Supported Catalysts and
Their Applications, Royal Society of Chemistry: Cambridge, UK,
2001.
Mojtahedi, M. M.; Abaee, M. S. In Handbook on Applications of
Ultrasound: Sonochemistry for Sustainability; Chen, D.; Sharma,
S. K.; Mudhoo, A., Eds.; CRC Press: New York, 2012.
10. Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629–
639.
11. Nasir Baig, R. B.; Varma, R. S. Chem. Soc. Rev. 2012, 41, 1559–
1584.
12. Wang, G.-W. Chem. Soc. Rev. 2013, 42, 7668–7700.
13. Zhu, S.-E.; Li, F.; Wang, G.-W. Chem. Soc. Rev. 2013, 42, 7535–
7570.
14. Blass. B. E. Tetrahedron 2002, 58, 9301–9320.
15. Pace, V.; Martínez, F.; Nova, C. I.; Fernández, M.; Sinisterra, J.
V.; Alcántara, A. R. Tetrahedron Lett. 2009, 50, 3050–3053.
16. Mizar, P.; Myrboh, B. Tetrahedron Lett. 2009, 50, 3088–3091.
17. Verziu, M.; Florea, M.; Simon, S.; Simon, V.; Filip, P.;
Parvulescu, V. I.; Hardacre, C. J. Catal. 2009, 263, 56–66.
18. Mizar, P.; Myrboh, B. Tetrahedron Lett. 2008, 49, 5283–5285.
19. Deshmukh, M. B.; Deshmukh, S. A.; Jagtap, S. S
Figure 1. Reusability of the catalyst.
In summary, this work represents a useful method for the
rapid synthesis of a diverse array of benzothiazinone compounds
under fairly mild conditions. Some previously reported studies
for the synthesis of 3a were compared with the current method
(Table 4). The present work showed very good performance in
comparison to many of the previously reported studies in terms
of yield, reaction conditions and time.
Indian J. Chem
46
–
20. Tawada, H.; Sugiyama, Y.; Ikeda, H.; Yamamoto, Y.; Meguro, K.
Chem. Pharm. Bull. 1990, 38, 1238–1245.
21. Dolzhenko, A. V.; Chui, W.-K. Heterocycles 2004, 63, 2623–
2626.
22. Molteni, V.; He, X.; Nabakka, J.; Yang, K.; Kreusch, A.; Gordon,
P.; Bursulaya, B.; Warner, I.; Shin, T.; Biorac, T.; Ryder, N. S.;
Goldberg, R.; Doughty, J.; He, Y. Bioorg. Med. Chem. Lett. 2004,
14, 1477–1481.
23. Zuo, H.; Li, Z.-B.; Ren, F.-K.; Falck, J. R.; Lijuan, M.; Ahn, C.;
Shin, D.-S. Tetrahedron, 2008, 64, 9669–9674.
24. Hori, M.; Kataoka, T.; Shimizu, H.; Imai, Y. Chem. Pharm. Bull.
1979, 27, 1973–1981.
25. Pramanik, A.; Roy, P. Tetrahedron lett. 2013, 54, 5243–5245.
26. Anderson, J. E.; Bell, S.; Best, W. M.; Drygala, P. F.; Watson, K.
G. Pestic. Sci. 1996, 46, 131–138.
Table 4. Comparison of the present procedure with selected
recent reported methods.
Entry Condition
Yield% (time)
40 (6 d)28
1
2
3
4
Et2O, Et3N, rt
[Omim][NO3], rt
98 (2 h)29
KF/Al2O3, IL, 85 C,
94 (2.5 h)30
1. NaOMe/ MeOH, RX, reflux 71- 80 (6 min)30
27. Sharifi, A.; Abaee, M. S.; Rouzgard, M.; Mirzaei M. Synth.
Commun. 2013, 43, 2079–2089.
28. Endo, T.; Noguchi, S.; Mukaiyama, T. Bull. Chem. Soc. Jpn.
1971, 44, 3424.
29. Sharifi, A.; Abaee, M.; Rouzgard, M.; Mirzaei, M.; Green. Chem.
Lett. 2012, 4, 649-698.
2. Basic alumina, MW, 100 C
5
6
7
NMP, DBU, MW, 180 C
SeO2/dioxane, MW/ 120 C,
KF/Al2O3, ball mill, rt
98 (4 min)31
82-89 (3 min)32
97 (30 min)33
30. Chhikara, B. S.; Tandon, V.; Mishra, A. K. Heterocycl. Commun.
2004, 10, 441.
31. Kamila, S.; Koh, B.; Khan, O.; Zhang, H.; Biehl, E. R. J.
Heterocyclic Chem. 2006, 43, 1641–1646.
32. Sawhney, S. N.; Sharma, P. K.; Bajaj, K.; Gupta, A., Indian. J.
Chem. B. Org. 1994, 33, 280-284.
Acknowledgments
The Ministry of Science, research and Technology of Iran is
acknowledged for partial financial assistance of this work.
33. Typical procedure: A 5.0 mL stainless steel vial was charged with
a mixture of 1 (1.0 mmol), 2 (1.2 mmol), KF/Al2O3 (160 mg, 1.0
mmol) and a 10 mm stainless steel ball. The vial was sealed with a
Teflon® gasket and the mixture was shaken at 20 Hz in an
oscillatory ball mill apparatus for the appropriate length of time.
After reaction completion, based on TLC, the mixture was diluted
with EtOAc (10 mL) and filtered to separate the catalyst. The
filtrate was concentrated under reduced pressure and if necessary,
purified by column chromatography using silica gel and
EtOAc/hexanes (1/10) as eluent. All products are known and their
identities were confirmed by comparing their 1H NMR spectra
with those previously reported.19,20,27,29,31,32
References and notes
1.
2.
3.
4.
5.
6.
Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and
Practice; Oxford University Press: Oxford, UK, 1998.
Tundo, P.; Perosa, A.; Zecchini, F. Methods and Reagents for
Green Chemistry; John Wiley & Sons: Hoboken, NJ, 2007.
Garay, A. L.; Pichon, A.; James, S. L. Chem. Soc. Rev. 2007, 36,
846–855.
Rodríguez, B.; Bruckmann, A.; Rantanen, T.; Bolm, C. Adv.
Synth. Catal. 2007, 349, 2213–2233.
Tanaka, K. Solvent-free Organic Synthesis; 2nd ed., Wiley-VCH:
Weinheim, 2009.
Supplementary Material
Clark, J. H.; Rhodes, C. N. Clean Synthesis Using Porous
Inorganic Solid Catalysts and Supported Reagents; Royal Society
of Chemistry: Cambridge, UK, 2000.
Supplementary data (Spectra of all products) associated with
this article can be found, in the online version.
7.
Sheldon, R. A.; van Bekkum, H. Fine Chemicals through
Heterogeneous Catalysis; Wiley-VCH: Weinheim, 2001.