Synthesis of 4H-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole 5-oxide and its N- and O-alkyl derivatives

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8577-8580

  Churakov, Aleksandr M ^b   Ioffe, Sema L ^a   Strelenko, Yuri A ^a   Tartakovsky, Vladimir A ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

OXADIAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 16144365212     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01992-2     Document Type: Article

References (15)

1. 1. Rezchikova, K. I.; Churakov, A. M.; Shlyapochnikov, V. A.; Tartakovsky, V. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, (8), 1825-1828 (Bull. Acad. Sci. USSR, Div. Chem. Sci. 1991, 40, 1615-1617).
2. 1. Rezchikova, K. I.; Churakov, A. M.; Shlyapochnikov, V. A.; Tartakovsky, V. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, (8), 1825-1828 (Bull. Acad. Sci. USSR, Div. Chem. Sci. 1991, 40, 1615-1617).
3. 2. For 2-hydroxytriazole, see ref. (a); N-alkyltriazole 2-oxides fused with benzene (ref. b) or pyridine ring (ref. c) were obtained by UV irradiation of appropriate N-alkyltriazole 3-oxides; (a) Kishida, H.; Shudo, A.; Sakamoto, N.; Fujimoto, H.; Umeda, K. Japan patent 05,222,006, 1993; Chem. Abstr. 1994, 120, 25611j;
4. 2. For 2-hydroxytriazole, see ref. (a); N-alkyltriazole 2-oxides fused with benzene (ref. b) or pyridine ring (ref. c) were obtained by UV irradiation of appropriate N-alkyltriazole 3-oxides; (a) Kishida, H.; Shudo, A.; Sakamoto, N.; Fujimoto, H.; Umeda, K. Japan patent 05,222,006, 1993; Chem. Abstr. 1994, 120, 25611j;
5. (b) Serve, M. P.; Feld, W. A.; Seybold, P. G.; Steppel, R. N. J. Heterocycl. Chem. 1975, 12, 811-812;
6. (c) Hubert, A. J.; Anthoine, G. Bull. Soc. Chim. Belges. 1969, 78, 553-560.
7. 3. Tselinskii, I. V.; Mel'nikova, S. F.; Vergizov, S. N. Zh. Org. Khim. 1981, 17, 1123-1124. Caution! Compound 6 as well as 8 - 14 and especially 7 should be handled as potentially explosive materials.
8. 4. The analytical and spectroscopic data of 7 completely agree with the structure suggested.
9. 5. Churakov, A. M.; Semenov, S. E.; Ioffe, S. L.; Strelenko, Yu, A.; Tartakovsky, V. A. Mendeleev Commun. 1995, 102-103.
10. 6. After we had begun this study, the thermal reaction of 2-(N-nitroso-N-alkylamino)-3-azido-1,4-naphtoquinones yielding 1-alkyl-1,2,3-triazole 2-oxide derivatives was published: Gornostaev, L. M.; Timoshkova, N. A.; Sakilidi, V. T. The Fifteenth International Congress of Heterocyclic Chemistry, Taipei, 1995, PO2-169.
11. 7. For closely related 5-phenyl-5H[1,2,3]-triazolo[4,5-c][1,2,5]oxadiazole see: Matsumoto, A.; Yoshida, M.; Simarnura, O. Bull. Chem. Soc. Jap. 1974, 47, 1493-1495; Benson, F. R. The High Nitrogen Compounds; Wiley; New York, 1984; pp. 93-95; for review on furazanes fused to five-membered rings see: A. B. Sheremetev A. B. J. Heterocyclic Chem. 1995, 32, 371-385.
12. 7. For closely related 5-phenyl-5H[1,2,3]-triazolo[4,5-c][1,2,5]oxadiazole see: Matsumoto, A.; Yoshida, M.; Simarnura, O. Bull. Chem. Soc. Jap. 1974, 47, 1493-1495; Benson, F. R. The High Nitrogen Compounds; Wiley; New York, 1984; pp. 93-95; for review on furazanes fused to five-membered rings see: A. B. Sheremetev A. B. J. Heterocyclic Chem. 1995, 32, 371-385.
13. 7. For closely related 5-phenyl-5H[1,2,3]-triazolo[4,5-c][1,2,5]oxadiazole see: Matsumoto, A.; Yoshida, M.; Simarnura, O. Bull. Chem. Soc. Jap. 1974, 47, 1493-1495; Benson, F. R. The High Nitrogen Compounds; Wiley; New York, 1984; pp. 93-95; for review on furazanes fused to five-membered rings see: A. B. Sheremetev A. B. J. Heterocyclic Chem. 1995, 32, 371-385.
14. 8. For the intramolecular reaction of diazonio oxide cation with tert-butylazoxy group resulting in benzo-1,2,3,4-tetrazine 1,3-dioxide see: Churakov, A. M.; Ioffe, S. L.; Tartakovsky, V. A. Mendeleev Commun. 1991, 101.
15. 9. For intermolecular reactions of this type see ref. 5.