Intramolecular cyclization of 1,2-bis(N-alkoxy-N-nitrosoamino)alkanes: A unique route to 4,5-dihydro-1,2,3-triazole 2-oxides

Synthesis

Volumn , Issue 5, 2000, Pages 681-690

  Khlestkin, Vadim K ^a   Mazhukin, Dmitrii G ^a   Tikhonov, Alexsei Ya ^a   Rybalova, Tatyana V ^a   Bagryanskaya, Irina Yu ^a   Gatilov, Yurii V ^a  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

1,2,3 triazole 2 oxides; 1,2 bis(nitrosohydroxylamines); 1,2 bis(N alkoxy N nitroso)amines; 1,2 bisalkoxyamines; Hererocycles; Intramolecular cyclization; Nitrogen; Nitrosation

Indexed keywords

ALKANE; HETEROCYCLIC COMPOUND; NITROGEN; OXIDE; TRIAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; MOLECULAR INTERACTION; NITROSATION; REACTION ANALYSIS;

EID: 0034115326     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6399     Document Type: Article

References (43)

1. Lindner, R.; Behrend, R. Liebigs Ann. Chem. 1893, 275, 133.
2. (a) Hickmann, E.; Hädicke, E.; Reuther, W. Tetrahedron Lett. 1979, 2457.
3. (b) Lamberton, A.H; Yusuf, H.M. J. Chem. Soc. Sect. C 1969, 397.
4. Axenrod, T.; Wieder, M.J.; Milne G.W.A. Tetrahedron Lett. 1969, 401.
5. Boese, A.B., Jr.; Jones, L.W.; Major, R.T. J. Am. Chem. Soc. 1931, 53, 3530.
6. Meesters, A.C.M.; Rueger, H.; Rajeswari, K.; Benn, M.H. Can. J. Chem. 1981, 59, 264.
7. (a) Kano, K.; Anselme, J.-P. Tetrahedron 1992, 48, 10075.
8. (b) Kano, K.; Anselme, J.-P. J. Org. Chem. 1993, 58, 1564.
9. (c) Kano, K.; Anselme, J.-P. Tetrahedron 1993, 49, 9453.
10. Maskill, H.; Meneer, L.D.; Smith, D.I. J. Chem. Soc., Chem. Commun. 1995, 18, 1855.
11. Hwu, J.R.; Yau, C.S.; Tsay, S.-C.; Ho, T.-I. Tetrahedron Lett. 1997, 38, 9001.
12. Feelish, M.; Stamler, J.S. In Methods in Nitric Oxide Research; Feelish, M., Stamler, J.S. Eds.; Wiley: Berlin 1996; p 71.
13. (a) Bamberger, E.; Ekecrantz, T. Ber. Dtsch. Chem. Ges. 1896, 29, 2412.
14. (b) George, M.V.; Kierstead, R.W.; Wright, G.F. Can. J. Chem. 1959, 37, 679.
15. (c) Zyusin, I.N.; Nechiporenko, G.N.; Golovina, N.I.; Trofimova, R.F.; Loginova, N.V. Russ. Chem. Bull. 1997, 46, 1421; Chem. Abstr. 1998, 128, 34546 and references cited therein.
16. (c) Zyusin, I.N.; Nechiporenko, G.N.; Golovina, N.I.; Trofimova, R.F.; Loginova, N.V. Russ. Chem. Bull. 1997, 46, 1421; Chem. Abstr. 1998, 128, 34546 and references cited therein.
17. Khlestkin, V.K.; Mazhukin, D.G.; Tikhonov, A.Ya.; Bagryanskaya, I.Yu.; Gatilov, Yu.V.; Utepbergenov, D.I.; Khramtsov, V.V.; Volodarsky, L.B. Tetrahedron Lett. 1996, 37, 5997.
18. (a) Hubert, A.J.; Anthione, G. Bull. Soc. Chim. Belg. 1969, 78, 553.
19. (b) Serve, M.P.; Feld, W.A.; Seybold, P.G.; Steppel, R.N. J. Heterocycl. Chem. 1975, 12, 811.
20. th Int. Congr. Heterocycl. Chem.: Taipei, 1995, PO2-169.
21. Miura, Y.; Takaku, S.; Nawata, Y.; Hamana, M. Heterocycles 1992, 34, 1491.
22. Churakov, A.M.; Ioffe, S.L.; Strelenko, Yu.A.; Tartakovsky, V.A. Tetrahedron Lett. 1996, 37, 8577.
23. Starchenkov, I.B.; Andrianov, V.G.; Mishnev, A.F. Chem. Heterocycl. Compd.(N.Y.)1998, 33, 1355; Chem. Abstr. 1998, 129, 202921.
24. Starchenkov, I.B.; Andrianov, V.G.; Mishnev, A.F. Chem. Heterocycl. Compd.(N.Y.)1998, 33, 1355; Chem. Abstr. 1998, 129, 202921.
25. Mazhukin, D.G.; Tikhonov, A.Ya.; Volodarsky, L.B.; Konovalova, E.P.; Tikhonova, L.A.; Bagryanskaya, I.Yu.; Gatilov, Yu.V. Russ. Chem. Bull. 1993, 42, 851; Chem. Abstr. 1995, 123, 197958.
26. Mazhukin, D.G.; Tikhonov, A.Ya.; Volodarsky, L.B.; Konovalova, E.P.; Tikhonova, L.A.; Bagryanskaya, I.Yu.; Gatilov, Yu.V. Russ. Chem. Bull. 1993, 42, 851; Chem. Abstr. 1995, 123, 197958.
27. Lamchen, M.; Mittag, T.W. J. Chem. Soc., Sect. C 1966, 2300.
28. Bagryanskaya, I.Yu.; Rybalova, T.V.; Gatilov, Yu.V.; Khlestkin, V.K.; Mazhukin D.G. Acta Crystallogr., Sect. C 1998, 54, IUC9800073.
29. Kostyanovsky, R.G.; Rudchenko, V.F.; Shtamburg, V.G.; Chervin, I.I.; Nasibov, Sh.S. Tetrahedron 1981, 37, 4245.
30. (a) Woldman, Y.Yu.; Khramtsov, V.V.; Grigor'ev, I.A.; Kirilyuk, I.A.; Utepbergenov, D.I. Bioch. Biophys. Res. Commun. 1994, 202, 195.
31. (b) Ullman, E.F.; Call, L.; Osiecki, J.H. J. Org. Chem. 1970, 35, 3623.
32. (c) Akakike, T.; Yoshida, M.; Miyamoto, Y.; Sato, K.; Kohno, M.; Sasamoto, K.; Miyazaki, K.; Ueda, S.; Maeda, H. Biochemistry 1992, 32, 827.
33. (d) Joseph, J.; Kalyanaraman, B.; Hyde, J. S. Bioch. Biophys. Res. Commun. 1993, 192, 926.
34. Quast, H.; Hergenrother, T.; Banert, K.; Peters, E.-M.; Peters, K.; von Schnering, H.G. Chem. Ber. 1993, 126, 103.
35. Allen, F.A.; Kennard, O.; Watson, D.G.; Brammer, L.; Orpen, A.C.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
36. Kemmish, H.J.; Hamor, T.A. Acta Crystallogr., Sect. C (Cr. Str. Comm.) 1991, 47, 620.
37. Ullman, E.F.; Singh, P. J. Am. Chem. Soc. 1972, 94, 5077.
38. Mazhukin, D.G.; Khlestkin, V.K.; Tikhonov, A.Ya.; Volodarsky, L.B. Izv. Akad. Nauk, Ser. Khim. 1996, 925; Chem. Abstr. 1996, 125, 195030.
39. Mazhukin, D.G.; Khlestkin, V.K.; Tikhonov, A.Ya.; Volodarsky, L.B. Izv. Akad. Nauk, Ser. Khim. 1996, 925; Chem. Abstr. 1996, 125, 195030.
40. Sheldrick, G.M. Acta Crystallogr. 1990, A46, 467.
41. Sheldrick, G.M. Acta Crystallogr. 1993, A49 (Suppl.), C53.
42. Atomic coordinates, bond lengths and angles have been deposited at the Cambridge Crystallographic Data Center, University Chemical Laboratory, Lensfield Road, Cambridge, CB2 EW, England.
43. Schmidt, J.; Zinner, G. Arch. Pharm. (Weinheim) 1979, 312, 1019.