Sevil ÖZCAN, Zeynep EKMEKÇİ, Berk MÜJDE, Metin BALCI

Synthesis of fused tetrazolone derivatives

New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazolone derivative was formed.

Anahtar Kelimeler:

Tetrazolone, acyl azide, Curtius rearrangement, 1, 3-dipole, dipolarophile, 1, 3-dipolar cycloaddition

Synthesis of fused tetrazolone derivatives

Keywords:

Tetrazolone, acyl azide, Curtius rearrangement, 1, 3-dipole, dipolarophile, 1, 3-dipolar cycloaddition,

PDF

___

1. (a) Nagendra, G.; Narendra, N.; Sureshbabu, Vommina V. Indian J. Chem. Section B. 2012, 51B, 486–492; (b) Bahadoor, A.; Castro, A. C.; Chan, L. K.; Keaney, G. F.; Nevalainen, M.; Nevalainen, V.; Peluso, S.; Snyder, D. A.; Tibbitts, T. T. PCT Int. Appl. 2011, WO 2011140190 A1 20111110; (c) Alawode, O. E.; Robinson, C.; Rayat, S. J. Org. Chem. 2011, 76, 216–222; (d) Gundugola, A. S.; Chandra, K. L.; Perchellet, E. M.; Waters, A. M.; Perchellet, J.-P. H.; Rayat, S. Bioorg. Med. Chem. 2010, 20, 3920–3924; (e) Zarubaev, V. V.; Golod, E. L.; Anfimov, P. M.; Shtro, A. A.; Saraev, V. V.; Gavrilov, A. S.; Logvinov, A. V.; Kiselev, O. I. Bioorg. Med. Chem. 2010, 18, 839–848; (f) Logvinov, A. V.; Polyakova, I. N.; Golod, E. L. Rus. J. Gen. Chem. 2009, 79, 2220–2229; (g) Holt, J.; Fiksdahl, A. J. Heterocycl. Chem. 2007, 44, 375–379; (h) Egorova, N. G.; Artamonova, T. V.; Hrabalek, A.; Koldobskii, G. I. Rus. J. Org. Chem. 2005, 41, 1399–1401.
2. Luo, Y-P.; Lin, L.; Yang, G.-F. J. Heterocycl. Chem. 2007, 44, 937–943.
3. (a) Kathleen, M. P.; Lawrenceville, N. J. US Patent, 4,913,724, 1990; (b) Yanagi, A.; Watanabe, Y.; Narabu, S. US Patent, 5,530,135, 1996.
4. (a) Goto, T.; Ito, S.; Yanagi, A.; Watanabe, Y.; Yasui, K. Weed. Biol. Manag. 2002, 2, 18–24. (b) Y.-P. L.; Guang-Fu. Y. Bioorg. Med. Chem. 2007, 15, 1716–1724.
5. (a) Theodoridis, G.; Hotzman, F. W.; Scherer, L. W.; Smith, B. A.; Tymonko, J. M.; Wyle, M. J. Pestic. Sci. 1990, 30, 259–274. (b) Theodororidis, G. PCT Int. Appl. WO 85 01, 939 (CI.C07D257/04); Chem. Abstr. 103 (1985) 141977f.
6. Horwitz, J. P.; Fisher B. E.; Tomazevski, A. J. J. Am. Chem. Soc. 1959, 81, 3076–3079.
7. Quast, H.; Nahr, U. Chem. Ber. 1983, 116, 3427–3437.
8. Vandensavel, J.-M.; Smets, G.; Labbe, G., J. Org. Chem. 1973, 38, 675–678.
9. Tsuge, O.; Urano S.; Oe, K. J. Org. Chem. 1980, 45, 5130–5113.
10. Toselli, M.; Zanirato, P. J. Chem. Soc. Perkin Trans. 1 1992, 1101–1104.
11. Salama, A. T.; Elmorsy, S. S.; Khalil, A.-G. M.; Ismail, M. A. Chem. Lett. 2011, 40, 1149–1151.
12. Deliomeroglu, M. K.; Ozcan, S.; Balci, M. Arkivoc 2010, 2, 148–160.
13. (a) Ozcan, S.; Sahin, E.; Balci, M. Tetrahedron Lett. 2007, 48, 2151–2154; (b) Ozcan, S.; Balci, M. Tetrahedron 2008, 64, 5531–5540.
14. (a) Goodridge, R. J.; Hambley, T. W.; Ridley, D. D. Aust. J. Chem. 1986, 39, 591−604. (b) Hall, H. K., Jr; Nogues, P.; Rhoades, J. W.; Sentman, R. C.; Detar, M. J. Org. Chem. 1982, 47, 1451−1455; (c) Ekmekci, Z.; Balci, M. Eur. J. Org. Chem. 2012, 4988–4995.
15. Koza, G.; Ozcan, S.; Sahin, E.; Balci, M. Tetrahedron 2009, 65, 5973–5976
16. Kita, Y.; Akai, S.; Ajimura, N.; Yoshigi, M.; Tsugoshi, T.; Yasuda, H.; Tamura, Y. J. Org. Chem. 1986, 51, 4150–4158.
17. Ozcan, S.; Dengiz, C.; Deliomeroglu, M. K.; Sahin, E.; Balci, M. Tetrahedron Lett. 2011, 52, 1495–1497.
18. Aluni, N. I.; Mark, P. K.; Allen, B. P. From PCT Int. Appl., 2006067444, 29 Jun 2006.
19. (a) Lamblin, M.; Couture, A.; Deniau, E.; Grandclaudon, P. Synthesis 2006, 1333–1338; (b) Kilikli, A. A.; Dengiz, C.; Ozcan, S.; Balci, M. Synthesis 2011, 3697–3705.