Synthesis of Novel Dispiro 1,4-Benzothiazine Hybrid Heterocycles Through 1,3-Dipolar Cycloaddition

REFERENCES

• (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; A. Padwa (Ed.); Wiley-Interscience: New York, 1984; Vols. 1 and 2; (b) Padwa, A. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming (Eds.); Pergamon: Oxford, 1991; Vol. 4; (c) Urdemann, M. W.; Christoffers, J. Tetrahedron 2014, 70, 4640–4644; (d) de Souza, U. M.; de Assis, F. F.; Carvalho, C. M. B.; Cavaleiro, J. A. S.; Brocksom, T. J.; de Oliveira, K. T. Tetrahedron Lett. 2014, 55, 1491–1495; (e) Salahi, F.; Taghizadeh, M. J.; Arvinnezhad, H.; Moemeni, M.; Jadidi, K.; Notash, B.; Pramanika, M. M. D.; Kant, R.; Rastogi, N. Tetrahedron Lett. 2014, 55, 1515–1518; (f) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863–909.
   Google Scholar
• (a) Salahi, F.; Taghizadeh, M. J.; Arvinnezhad, H.; Moemeni, M.; Jadidi, K.; Notash, B. Tetrahedron Lett. 2014, 55, 1515–1518; (b) Llompart, D. F.; Sarotti, A. M.; Corne, V.; Suárez, A. G.; Spanevello, R. A.; Echeverría, G. A.; Piro, O. E.; Castellano, E. E. Tetrahedron Lett. 2014, 55, 2394–2397; (c) Moghadda, F. M.; Khodabakhshi, M. R.; Ghahremannejad, Z.; Foroushani, B. K.; Ng, S. W. Tetrahedron Lett. 2013, 54, 2520–252; (d) Rao, J. N. S.; Raghunathan, R. Tetrahedron Lett. 2013, 54, 6568–6573; (e) Korotaev, V. Y.; Barkov, A. Y.; Moshkin, V. S.; Matochkina, E. G.; Kodess, M. I.; Sosnovskikh, V. Y. Tetrahedron 2013, 69, 8602–8608; (f) Chandraprakash, K.; Sankaran, M.; Uvarani, C.; Shankar, R.; Ata, A.; Dallemer, F.; Mohan, P. S. Tetrahedron Lett. 2013, 54, 3896–3901.
   Web of Science ®Google Scholar
• (a) Ball-Jones, N. R.; Badillo, J. J.; Franz, A. K. Org. Biomol. Chem. 2012, 10, 5165–5181; (b) Kulkarni, M. G.; Dhondge, A. P.; Chavhan, S. W.; Borhade, A. S.; Shaikh, Y. B.; Birhade, D. R.; Desai, M. P.; Dhatrak, N. R. Beilstein J. Org. Chem. 2010, 6, 876–879; (c) Pellegrini, C.; Weber, M.; Borschberg, H.-J. Helv. Chim. Acta 1996, 79, 151–168.
   PubMed Web of Science ®Google Scholar
• (a) Jiang, H.; Zhao, J.; Han, X.; Zhu, S. Tetrahedron 2006, 62, 11008–11011; (b) Coutouli, A. E.; Lianis, P.; Mitakou, M.; Giannoulis, A.; Nowak, J. Tetrahedron 2006, 62, 1494–1501; (c) Gomes, P. J. S.; Nunes, C. M.; Pais, A. A. C. C.; Pinho e Melo, T. M. V. D.; Arnaut, L. G. Tetrahedron Lett. 2006, 47, 5475–5479.
   Web of Science ®Google Scholar
• Abou-Gharbia, M. A.; Doukas, P. H. Heterocycles 1979, 12, 637–640.
   Web of Science ®Google Scholar
• Kornett, M. J.; Thio, A. P. J. Med. Chem. 1976, 19, 892–898.
   PubMed Web of Science ®Google Scholar
• Lundahl, K.; Schut, J.; Schlatmann, J. L. M. A.; Paerels, G. B.; Peters, A. J. Med. Chem. 1972, 15, 129–132.
   PubMed Web of Science ®Google Scholar
• Ajani, O. O. Arch. Pharm. Chem. Life Sci. 2012, 345, 841–851.
   PubMed Web of Science ®Google Scholar
• (a) Warren, B. K.; Knaus, E. E. Eur. J. Med. Chem. 1987, 22, 411–415; (b) Dubey, S. K.; Seda, J. M.; Knaus, E. E. Eur. J. Med. Chem. 1984, 19, 371–372.
   Web of Science ®Google Scholar
• (a) Jacquot, Y.; Bermont, L.; Giorgi, H.; Refouvelet, B.; Adessi, G. L.; Daubrosse, E.; Xicluna, A. Eur. J. Med. Chem. 2001, 36, 127–136; (b) Gupta, R. R.; Dev, P. K.; Sharma, M. L.; Rajoria, C. M.; Gupta, A.; Nyati, M. Anticancer Drugs 1993, 4, 589–592.
   PubMed Web of Science ®Google Scholar
• (a) Schiaffella, F.; Macchiarulo, A.; Milanese, L.; Vecchiarelli, A.; Fringuelli, R. Bioorg. Med. Chem. 2006, 14, 5196–5203; (b) Fringuelli, R.; Schiaffella, F.; Bistoni, F.; Pitzurra, L.; Vecchiarelli, A. Bioorg. Med. Chem. 1998, 6, 103–108.
   PubMed Web of Science ®Google Scholar
• (a) Armenise, D.; Muraglia, M.; Florio, M. A.; De Laurentis, N.; Rosato, A.; Carrieri, A.; Corbo, F.; Franchini, C. Arch. Pharm. 2012, 345, 407–416; (b) Sabatini, S.; Kaatz, G. W.; Rossolini, G. M.; Brandim, D.; Fravolini, A. J. Med. Chem. 2008, 51, 4321–4330; (c) Rathore, B. S.; Kumar, M. Bioorg. Med. Chem. 2006, 14, 5678–5682.
   PubMed Web of Science ®Google Scholar
• Coughlin, S. A.; Danz, D. W.; Robinson, R. G.; Klingbeil, K. M.; Wentland, M. P.; Corbett, T. H.; Waud, W. R.; Zwelling, L. A.; Altschuler, E.; Bales, E.; Rake, J. B. Biochem. Pharmacol. 1995, 50, 111–122.
   PubMed Web of Science ®Google Scholar
• Hasegawa, K.; Ito, S.; Inoue, S.; Wakamatsu, K.; Ozeki, H.; Ishiguro, I. Biochem. Pharmacol. 1997, 53, 1435–1444.
   PubMed Web of Science ®Google Scholar
• Schwarzl, I.; Stark, U.; Brodmann, M.; Haiden, U.; Tritthart, H. A.; Stark, G. J. Cardiovasc. Pharmacol. 2000, 35, 309–314.
   PubMed Web of Science ®Google Scholar
• Pawar, Y.; Sonaware, A.; Nagle, P.; Mahulikar, P.; More, D. Int. J. Curr. Pharm. Res. 2011, 3, 47–51.
   Google Scholar
• Munde, S. B.; Bondge, S. P.; Bhingolikar, V. E.; Mane, R. A. Green Chem. 2003, 5, 278–279.
   Web of Science ®Google Scholar
• (a) Sivakumar, S.; Ranjith Kumar, R.; Ali, M. A.; Choon, T. S. Eur. J. Med. Chem. 2013, 65, 240–248; (b) Kanchithalaivan, S.; Anusha Rani, M.; Ranjith Kumar, R. Synth. Commun. 2014, 44(21), 3122–3129.
   PubMed Web of Science ®Google Scholar
• Peddinti, R. K.; Choudhary, G. Green Chem. 2011, 13, 3290–3299.
   Web of Science ®Google Scholar
• Crystallographic data (excluding structure factors) for compound 12b has been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 1021459. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0) 1223 762911 or e-mail: [email protected]].
   Google Scholar