Organometallic synthesis in the furazan series. 4. Reactions of azofurazans with organolithium compounds

Russian Chemical Bulletin

Volumn 53, Issue 3, 2004, Pages 615-621

  Sheremetev, A B ^a   Ivanova, E A ^a   Shatunova, E V ^a   Dmitriev, D E ^a   Kuz'mina, N E ^b  

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

^b KURNAKOV INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Russian Federation)

Author keywords

azofurazans; electrophilic addition; organolithium compounds; redox reaction; X ray diffraction study

Indexed keywords

1 BUTYL 1,2 BIS(4 METHOXYFURAZAN 3 YL)HYDRAZINE; 1 BUTYL 2 [4 (1,4 DIOXADECYL)FURAZAN 3 YL] 1 (4 HYDROXYFURAZAN 3 YL)HYDRAZINE; 1,2 BIS(4 METHOXYFURAZAN 3 YL) 1 (4 METHYLFURAZAN 3 YLMETHYL)HYDRAZINE; 1,2 BIS(4 METHOXYFURAZAN 3 YL)HYDRAZINE; 2 BUTYL 2 [4 (1,4 DIOXADECYL)FURAZAN 3 YL] 1 (4 HYDROXY 3 FURAZANYL)HYDRAZINE; 3,4 DIMETHYLFURAZAN; 4,4 DIMETHOXYAZOFURAZAN; AZOFURAZAN DERIVATIVE; FURAZAN DERIVATIVE; HYDRAZOFURAZAN; METHYLFURAN DERIVATIVE; ORGANOLITHIUM COMPOUND; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION REDUCTION REACTION;

EID: 4043064328     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUCB.0000035645.16537.ea     Document Type: Article

References (37)

1. A. B. Sheremetev and E. A. Ivanova, Izv. Akad. Nauk, Ser. Khim., 2003, 1910 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2017].
2. A. B. Sheremetev and E. A. Ivanova, Izv. Akad. Nauk, Ser. Khim., 2003, 1910 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2017].
3. Metody elementoorganicheskoi khimii [Methods of Organometallic Chemistry], Eds. T. V. Talalaev and K. A. Kocheshkov, Nauka, Moscow, 1971, 2, p. 873 (in Russian).
4. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
5. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
6. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
7. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
8. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
9. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
10. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
11. A. P. Grekov, Organicheskaya khimiya gidrazina [Organic Chemistry of Hydrazine], Tekhnika, Kiev, 1966 (in Russian); C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, Ronald Press, New York, 1966, 115 pp.; The Chemistry of Hydrazo, Azo and Azoxy Groups (The Chemistry of Functional Groups), Ed. S. Patai, J. Wiley and Sons, London, 1975, 1100 pp.; B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Khimiya organicheskikh proizvodnykh gidrazina [Chemistry of Organic Derivatives of Hydrazine], Khimiya, Leningrad, 1979, 224pp. (in Russian); N. V. Korovin, Gidrazin [Hydrazine], Khimiya, Moscow, 1980, 272 pp. (in Russian); U. Jensen-Korte and N. Mueller, in Methoden der organischen Chemie (Houben-Weyl), Ed. D. Klamann, Thieme, Stuttgart, 4th Ed., 1990, 16a, 425-648; P. R. Huddleston and I. G. C. Coutts, in Comprehensive Organic Functional Group Transformations, Eds. A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon-Elsevier, Oxford, 1995, 2, 371-383; U. Ragnarsson, Chem. Soc. Rev., 2001, 30, 205.
12. A. Yu. Sizov and A. B. Sheremetev, Izv. Akad. Nauk, Ser. Khim., 1992, 365 [Bull. Russ. Acad. Sci., Div. Chem. Sci., 1992, 41, 281 (Engl. Transl.)].
13. A. Yu. Sizov and A. B. Sheremetev, Izv. Akad. Nauk, Ser. Khim., 1992, 365 [Bull. Russ. Acad. Sci., Div. Chem. Sci., 1992, 41, 281 (Engl. Transl.)].
14. E. T. Apasov, A. B. Sheremetev, B. A. Dzhetigenov, A. V. Kalinin, and V. A. Tartakovskii, Izv. Akad. Nauk, Ser. Khim., 1992, 1916 [Bull. Russ. Acad. Sci., Div. Chem. Sci., 1992, 41, 1500 (Engl. Transl.)].
15. E. T. Apasov, A. B. Sheremetev, B. A. Dzhetigenov, A. V. Kalinin, and V. A. Tartakovskii, Izv. Akad. Nauk, Ser. Khim., 1992, 1916 [Bull. Russ. Acad. Sci., Div. Chem. Sci., 1992, 41, 1500 (Engl. Transl.)].
16. A. B. Sheremetev, E. A. Ivanova, A. Yu. Sizov, V. O. Kulagina, D. E. Dmitriev, and Yu. A. Strelenko, Izv. Akad. Nauk, Ser. Khim., 2003, 651 [Russ. Chem. Bull., Int. Ed., 2003, 52, 679].
17. A. B. Sheremetev, E. A. Ivanova, A. Yu. Sizov, V. O. Kulagina, D. E. Dmitriev, and Yu. A. Strelenko, Izv. Akad. Nauk, Ser. Khim., 2003, 651 [Russ. Chem. Bull., Int. Ed., 2003, 52, 679].
18. G. Ponzio and G. Ruggeri, Gazz. Chim. Ital., 1923, 53, 297.
19. G. Ponzio and L. Avogadro, Gazz. Chim. Ital., 1923, 53, 318.
20. E. Durio and S. Dugone, Gazz. Chim. Ital., 1936, 66, 139.
21. Pat. US 6388087, 2002; Chem. Abstr., 2002, 136, 371892.
22. D. Chavez, L. Hill, M. Hiskey, and S. Kinkead, J. Energetic Materials, 2000, 18, 219.
23. A. B. Sheremetev, N. N. Makhova, and W. Friedrichsen, Adv. Heterocycl. Chem., 2001, 78, 65.
24. A. B. Sheremetev, O. V. Kharitonova, E. V. Mantseva, V. O. Kulagina, E. V. Shatunova, N. S. Aleksandrova, T. M. Mel'nikova, E. A. Ivanova, D. E. Dmitriev, V. A. Eman, I. L. Yudin, V. S. Kuz'min, Yu. A. Strelenko, T. S. Novikova, O. V. Lebedev, and L. I. Khmel'nitskii, Zh. Org. Khim., 1999, 35, 1555 [Russ. J. Org. Chem., 1999, 35, 1525 (Engl. Transl.)].
25. A. B. Sheremetev, O. V. Kharitonova, E. V. Mantseva, V. O. Kulagina, E. V. Shatunova, N. S. Aleksandrova, T. M. Mel'nikova, E. A. Ivanova, D. E. Dmitriev, V. A. Eman, I. L. Yudin, V. S. Kuz'min, Yu. A. Strelenko, T. S. Novikova, O. V. Lebedev, and L. I. Khmel'nitskii, Zh. Org. Khim., 1999, 35, 1555 [Russ. J. Org. Chem., 1999, 35, 1525 (Engl. Transl.)].
26. A. B. Sheremetev and O. V. Kharitonova, Mendeleev Commun., 1992, 157.
27. A. B. Sheremetev, E. V. Shatunova, B. B. Averkiev, D. E. Dmitriev, V. A. Petukhov, and M. Yu. Antipin, Heteroatom Chem., 2004, 15, 131.
28. L. Chertanova, C. Pascard, and A. Sheremetev, Supramolec. Chem., 1993, 3, 71.
29. A. B. Sheremetev and E. V. Shatunova, Tez. dokl II Moskovskoi konf. po mezhfaznomu katalizu [Abstrs. of Papers, II Moscow Conf. on Phase Trasnfer Catalysis], Moscow, 1994, 70 (in Russian); E. V. Shatunova and A. B. Sheremetev, IX Eur. Symp. on Organic Chemistry (Warszawa, June 18-23, 1995), Warszawa (Poland), PA 115, 184.
30. A. B. Sheremetev and E. V. Shatunova, Tez. dokl II Moskovskoi konf. po mezhfaznomu katalizu [Abstrs. of Papers, II Moscow Conf. on Phase Trasnfer Catalysis], Moscow, 1994, 70 (in Russian); E. V. Shatunova and A. B. Sheremetev, IX Eur. Symp. on Organic Chemistry (Warszawa, June 18-23, 1995), Warszawa (Poland), PA 115, 184.
31. Yu. A. Strelenko, A. B. Sheremetev, and L. I. Khmel'nitskii, Khim. Geterotsikl. Soedin., 1992, 1101 [Chem. Heterocycl. Compd., 1992, 927 (Engl. Transl.)].
32. Yu. A. Strelenko, A. B. Sheremetev, and L. I. Khmel'nitskii, Khim. Geterotsikl. Soedin., 1992, 1101 [Chem. Heterocycl. Compd., 1992, 927 (Engl. Transl.)].
33. D. E. Dmitriev, Yu. A. Strelenko, and A. B. Sheremetev, Izv. Akad. Nauk, Ser. Khim., 2002, 277 [Russ. Chem. Bull., Int. Ed., 2002, 51, 290].
34. D. E. Dmitriev, Yu. A. Strelenko, and A. B. Sheremetev, Izv. Akad. Nauk, Ser. Khim., 2002, 277 [Russ. Chem. Bull., Int. Ed., 2002, 51, 290].
35. Yu. A. Strelenko, O. A. Rakitin, T. I. Godovikova, and L. I. Khmel'nitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 2852 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36 (Engl. Transl.)].
36. Yu. A. Strelenko, O. A. Rakitin, T. I. Godovikova, and L. I. Khmel'nitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 2852 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36 (Engl. Transl.)].
37. G. M. Sheldrick, SHELX93, University of Göttingen, Göttingen (Germany), 1993.