Furoxano[3,4-b]pyrazines: The first synthesis and x-ray structure

Journal of Heterocyclic Chemistry

Volumn 42, Issue 4, 2005, Pages 691-694

  Yudin, Igor L ^a   Sheremetev, Aleksei B ^a   Averkiev, Boris B ^b   Antipin, Mikhail Yu ^b  

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

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

2 ALKOXY 3,5 DINITRO 6 CHLOROPYRAZINE; 2 CHLORO 3 NITROPYRAZINE; 4H 6 ETHOXYFUROXANO[3,4 B]PYRAZIN 5 ONE; 4H 6 METHOXYFUROXANO[3,4 B]PYRAZIN 5 ONE; 4H 6 PROPOXYFUROXANO[3,4 B]PYRAZIN 5 ONE; 6 METHOXY 5 NITROFUROXANO[3,4 B]PYRAZIN; KETONE DERIVATIVE; PYRAZINE DERIVATIVE; SODIUM AZIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 19644376381     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570420432     Document Type: Article

References (25)

1. A. Gasco, G. Rua, E. Menziani, G. M.Nano and G. Tappi, J. Heterocyclic Chem., 6, 769 (1969).
2. D. N. Nicolaides and J. K. Gallos. Synthesis, 638 (1981).
3. R. L. Willer and D. W. Moore, J. Org. Chem., 50, 5123 (1985).
4. J. K. Gallos, P. S. Lianis and D. N. Nicolaides, J. Heterocyclic Chem., 26, 1415 (1989).
5. A. B. Sheremetev and I. L. Yudin, Usp. Khim., 72, 93 (2003) (in Russian)
6. [Russ. Chem. Rev. (Engl. Transl.), 72, 87 (2003)].
7. [a] A. B. Sheremetev, I. L. Yudin, N. N. Makhova, I. V. Ovchinnikov and D. B. Lempert, In Proc. 33st International Annual Conference of ICT - Energetic Materials: Synthesis, Production, and Application., 2002, Karlsruhe, FRG, pp 128/1-12;
8. [b] I. L. Yudin and A. B. Sheremetev, In All-Russian Conference "Energy Condensed Systems", 2002, Chernogolovka, Moscow-Yanus'K, 2002, pp 108-109 (in Russian);
9. th International Annual Conference of ICT - Energetic Materials: Reactions of Propellants, Explosives and Pyrotechnics, 2004, Karlsruhe, FRG.
10. For reviews on fused furoxan synthesis, see: [a] A. B. Sheremetev, J. Heterocyclic Chem., 32, 371 (1995);
11. nd Ed. Nauka, Moscow, 1996 (in Russian);
12. nd Ed. Nauka, Moscow, 1996 (in Russian);
13. [d] R. M. Paton, In Comprehensive Heterocyclic Chemistry, Vol. 4, A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, eds, Pergamon Press, Oxford, 1996, pp 229;
14. [e] A. B. Sheremetev, Usp. Khim., 68, 154 (1999) (in Russian)
15. [Russ. Chem. Rev., (Engl. Transl.) 68, 137 (1999)].
16. F. Terrier. Nucleophilic Aromatic Displacement: The Influence of the Nitro Group.- Organic Nitro Chemistry Series, VCH Publishers, Weinheim, 1991, 460 pp.
17. V. L. Rusinov and O. N. Chupakhin, Nitroazines. Moscow, Nauka, 1991, pp 10 (in Russian).
18. [a] V. A. Tartakovskii, O. P. Shitov, I. L. Yudin and V. A. Myasnikov, USSR Patent 1703645 (1991);
19. [b] I. L. Yudin, A. B. Sheremetev, O. P. Shitov and V. A. Tartakovskii, Mendeleev Commun., 196 (1995);
20. [c] B. B. Averkiev, M. Yu. Antipin, I. L. Yudin and A. B. Sheremetev, J. Mol. Struct., 606, 139 (2002).
21. C. Addicott, M. W. Wong and C. Wentrup, J. Org. Chem., 67, 8538 (2002) and references therein.
22. Following literature analogies the isomers 9′a-c are more preferable. For reviews that deal with tautomerizm of furoxans, see: ref. [7b,7d,7e].
23. For view of an extraordinary susceptibility of polynitroazines to ubiquitous environmental contaminants such as water, see: R. D. Chapman, W. S. Wilson, J. W. Fronabarger, L. H. Merwin and G. S. Ostrom, Thermochim. Acta, 384, 229 (2002).
24. A. S. Batsanov and Yu. T. Struchkov, Zh. Strukt. Khim., 26, 65 (1985) (in Russian).
25. G. M. Sheldrick, SHELXTL-97, Version 5.10, Bruker AXS Inc., Madison, WI-53719, USA.