The first example of the synthesis of 1-aminoindole derivatives by the Nenitzescu reaction

Russian Chemical Bulletin

Volumn 53, Issue 12, 2004, Pages 2834-2839

  Lyubchanskaya, V M ^a   Savina, S A ^a   Alekseeva, L M ^a   Shashkov, A S ^b   Chernyshev, V V ^c   Granik, V G ^a  

^a State Scientific Center of Antibiotics   (Russian Federation)

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

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

1 aminoindoles; Nenitzescu reaction; Nitro enehydrazines; X ray diffraction analysis

Indexed keywords

1 ACETYLAMINO 6 HYDROXY 2 METHYL 3 NITROINDOLE; 1 AMINO 6 HYDROXY 2 METHYL 3 NITROINDOLE; 1 BENZYLIDENEAMINO 6 HYDROXY 2 METHYL 3 NITRO 1H INDOLE; 6 ACETOXY 1 ACETYLAMINO 2 METHYL 3 NITROINDOLE; 6 ACETOXY 1 BENZYLIDENEAMINO 2 METHYL 3 NITRO 1H INDOLE; HYDRAZINE DERIVATIVE; INDOLE DERIVATIVE; NITRO DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DEACYLATION; DRUG SYNTHESIS; HYDROGEN BOND; HYDROLYSIS; NENITZESCU REACTION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 21644462147     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-005-0198-3     Document Type: Article

References (29)

1. B. A. Frontana-Uribe, C. Moinet, and L. Toupet, Eur. J. Org. Chem., 1999, 419.
2. F. Schwartz, U. Jahn, Th. Wagner-Jauregg, L. Zirngibl, and K. Thiele, Arzneim.-Forsch./Drug. Res., 1980, 30, 919.
3. Eur. Pat. 509 400; Chem. Abstr., 1992, 118, 101970.
4. Eur. Pat. 287 982; Chem. Abstr., 1989, 110, 114690.
5. J. T. Klein, L. Davis, G. E. Olsen, G. S. Wong, F. P. Huger, C. P. Smith, W. W. Petko, M. Cornfeldt, J. C. Wilker, R. D. Blitzer, E. Landau, V. Harautunian, L. L. Martin, and R. C. Effland, J. Med. Chem., 1996, 39, 570.
6. M. Somei and N. Natsume, Tetrahedron Lett., 1974, 461.
7. G. Sosnovsky and K. Purgstaller, Z. Naturforsch., 1989, 44B, 582.
8. D. I. Haddlesey, P. A. Mayor, and S. S. Szinai, J. Chem. Soc., 1964, 5269.
9. L. S. Besford and J. M. Bruce, J. Chem. Soc., 1964, 4037.
10. F. Schwartz and Th. Wagner-Jauregg, Helv. Chim. Acta, 1968, 51, 1919.
11. V. M. Lyubchanskaya, L. M. Alekseeva, S. A. Savina, A. S. Shashkov, and V. G. Granik, Mendeleev Commun., 2004, 73.
12. G. R. Allen, Organic Reactions, Wiley Interscience, New York, 1973, 20, 337.
13. V. G. Granik, V. M. Lyubchanskaya, and T. I. Mukhanova, Khim.-Farm. Zh., 1993, 27, No. 6, 37
14. [Pharm. Chem. J., 1993, 27, No. 6 (Engl. Transl.)].
15. V. G. Granik, Organicheskaya khimiya [Organic Chemistry], Vuzovskaya kniga, Moscow, 2003, p. 191 (in Russian).
16. V. M. Lyubchanskaya, L. M. Alekseeva, S. A. Savina, A. S. Shashkov, and V. G. Granik, Izv. Akad. Nauk, Ser. Khim., 2002, 1736
17. [Russ. Chem. Bull., Int. Ed., 2002, 51, 1886].
18. T. I. Mukhanova, E. K. Panisheva, V. M. Lyubchanskaya, L. M. Alekseeva, Yu. N. Sheinker, and V. G. Granik, Tetrahedron, 1997, 53, 177.
19. R. F. Abdulla and R. S. Brinkmayer, Tetrahedron, 1979, 35, 1675.
20. V. M. Lyubchanskaya, L. M. Alekseeva, and V. G. Granik, Khim. Geterotsikl. Soedin., 1992, 40
21. [Chem. Heterocycl. Comp., 1992, 28, 34 (Engl. Transl.)].
22. M. Somei and Y. Kurizuka, Chem. Lett., 1979, 127.
23. N. I. Mikerova, L. M. Alekseeva, E. K. Panisheva, Yu. N. Sheinker, and V. G. Granik, Khim. Geterotsikl. Soedin., 1990, 324
24. [Chem. Heterocycl. Comp., 1990, 26 (Engl. Transl.)].
25. L. M. Alekseeva, T. I. Mukhanova, E. K. Panisheva, O. S. Anisimova, K. F. Turchin, A. V. Komkov, V. A. Dorokhov, and V. G. Granik, Izv. Akad. Nauk, Ser. Khim., 1999, 160
26. [Russ. Chem. Bull., 1999, 48, 160 (Engl. Transl.)].
27. U. Kuklaender, Arch. Pharm. (Weinheim), 1977, 310, 385.
28. V. V. Chernyshev and H. Schenk, Z. Kristallogr., 1998, 213, 1.
29. V. B. Zlokazov and V. V. Chernyshev, J. Appl. Crystallogr., 1992, 25, 447.