Efficient preparation of N′,N″-1H-isoindole-1,3-diylidenedicarbohydrazides via 1,1,3-trichloro-1H-isoindole, and their characterization

Tetrahedron

Volumn 65, Issue 31, 2009, Pages 6218-6225

  Hordiyenko, Olga V ^a   Rudenko, Igor V ^a   Biitseva, Angelina V ^a   Turov, Aleksandr V ^a   Arrault, Axelle ^b   Brosse, Nicolas ^b   Fabre, Olivier ^b   Jamart Grégoire, Brigitte ^b   Zubatyuk, Roman I ^c   Shishkin, Oleg V ^c  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b LAB DE CHIM PHYS MACROMOLECULAIRE   (France)

^c INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

Author keywords

1H Isoindole; Carbohydrazides; NMR spectroscopy; Structure elucidation; X ray diffraction

Indexed keywords

DI TERT BUTYL 2,2' (1H ISOINDOLE 1,3 DIYLIDENE)DIHYDRAZINECARBOXYLATE; HYDRAZIDE DERIVATIVE; ISOINDOLE DERIVATIVE; N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBENZOHYDRAZIDE; N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBIS(2 BROMO BENZOHYDRAZIDE); N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBIS(2 CHLORO BENZOHYDRAZIDE); N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBIS(2 IODOBENZOHYDRAZIDE); N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBIS(2 METHYL PROPANOHYDRAZIDE); N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBIS(4 BROMO BENZOHYDRAZIDE); N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBIS(4 FLUORO BENZOHYDRAZIDE); N',N'' 1H ISOINDOLE 1,3 DIYLIDENEBIS(4 METHYL BENZOHYDRAZIDE); N',N'' 1H ISOINDOLE 1,3 DIYLIDENEDIACETOHYDRAZIDE; N',N'' 1H ISOINDOLE 1,3 DIYLIDENEDIADAMANTANE 1 CARBOHYDRAZIDE; N',N'' 1H ISOINDOLE 1,3 DIYLIDENEDIPYRIDINE 2 CARBOHYDRAZIDE; N',N'' 1H ISOINDOLE 1,3 DIYLIDENEDITHIOPHENE 2 CARBOHYDRAZIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PRODUCTIVITY; QUANTUM MECHANICS; SOLID STATE; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 67649378631     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.031     Document Type: Article

References (38)

1. Mashkovskii, M. D. Lekarstvennie sredstva. In 2 parts (in Russian). Novaya Volna: Vilnius, 1994; part 1, p 80, part 2, p 278.
2. Danilenko G.I., Rybalko S.L., Maksimov Yu.N., Baklan V.F., and Guzhova S.V. Pharm. Chem. J. 34 (2000) 23-24
3. Grant E.B., Guiadeen D., Singer M., Argentieri D., Hlasta D.J., and Wachter M. Bioorg. Med. Chem. Lett. 11 (2001) 2817-2820
4. Guzman C.M., Perez B.D., and Pino F. An. Quim. 72 (1976) 651-656
5. Giridhara R.K., Prakash K.M.M.S., Hussain R.K., and Venkata R.D. Acta Cienc., Indica, Chem. 10 (1984) 175-177
6. Jimenez M.A., Guzman C.M., and Pino F. Quim. Anal. (Madrid) 31 (1977) 307-311
7. Guzman C.M., Perez-Bendito D., and Pino F. Anal. Chim. Acta 83 (1976) 259-266
8. Callejon Mochon M., and Munoz Leyva J.A. Microchem. J. 34 (1986) 83-88
9. Hordiyenko O.V., Biitseva A.V., Kornilov M.Yu., Brosse N., Hocquet A., Jamart-Grégoire B., Shishkin O.V., and Zubatyuk R.I. Eur. J. Org. Chem. 12 (2006) 2833-2842
10. Wolf, W.; Vollmann, H. Bayer AG. DE Patent 941845, 1956;
11. Chem. Abstr. 53 (1959) 6251c
12. Elvidge J.A., and Redman A.P. J. Chem. Soc., Perkin Trans. 1 (1972) 2820-2822
13. Titkov, V. A.; Savitskaya, E. V.; Leina, T. F. USSR Patent 225881, 1972;
14. Chem. Abstr. 77 (1972) 126422x
15. Guzman C.M., Perez B.D., and Pino F. An. Quim. 70 (1974) 828-832
16. Negrebetskii V.V., Balitskaya O.V., and Kornilov M.Yu. Russ. J. Gen. Chem. 53 (1983) 2573-2586
17. Friedrichsen W., Traulsen T., Elguero J., and Katritzky A.R. Tautomerism of Heterocycles: Five-membered Rings with One Heteroatom. Advances in Heterocyclic Chemistry Vol. 76 (2000), Academic Press, San Diego, CA p 129
18. Licandro E., and Perdicchia D. Eur. J. Org. Chem. (2004) 665-675
19. Pihlaja K., Simeonov M.F., and Fülöp F. J. Org. Chem. 62 (1997) 5080-5088
20. Bayer AG. GB Patent 704595, 1954;
21. Chem. Abstr. 49 (1955) 7001
22. Vollmann, H.; Baumann, F.; Bienert, B. U.S. Patent 2,701,252, 1955;
23. Chem. Abstr. 49 (1955) 53710
24. Kornilov M.Yu., and Makovetsky V.P. Dopov. Nats. Akad. Nauk Ukr., Ser. B 11 (1974) 1013-1019
25. Gordienko O.V., Negrebetskii V.V., Ivanchenko V.I., and Kornilov M.Yu. Russ. J. Gen. Chem. 59 (1989) 2771-2779
26. Sheldrick G.M. SHELX97. Programs for Crystal Structure Analysis (Release 97-2) (1997), University of Göttingen, Germany
27. Speck A.L. PLATON, A Multipurpose Crystallographic Tool (1998), Utrecht University, Utrecht, The Netherlands
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A. Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Gaussian: Pittsburgh, PA, 1998.
29. Becke A.D. J. Chem. Phys. A 98 (1993) 5648-5652
30. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200-206
31. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
32. Vosko S.H., Wilk L., and Nusair M. Can. J. Phys. 58 (1980) 1200-1211
33. Ditchfield R., Hehre W.J., and Pople J.A. J. Chem. Phys. 54 (1971) 724-728
34. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257-2261
35. Hariharan P.C., and Pople J.A. Mol. Phys. 27 (1974) 209-214
36. Gordon M.S. Chem. Phys. Lett. 76 (1980) 163-168
37. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213-222
38. Frisch M.J., Pople J.A., and Binkley J.S. J. Chem. Phys. 80 (1984) 3265-3269