Bruker Vector KBr ( 0,25 %). .
1 13 Bruker AM 400 (400,13 (1) 100,61 M (13) CDCl3 -d6 10% 25 . : Cl3 (δH 7,24 . . δ 76,90 . ) -d6 (δH 2,50 . . δ 39,50 . ). 13 J- (JMOD).
Sorbfil UV-254. . MN Kiselgel 60 (70-230 mesh)
.
4-[2,1,3]-1-
13,6 (0,1 ) [2,1,3]-1- 44,5 . 5-12º (20 ) d=1,5 (5 , 0,12 ), . 12º. 30 150 .
, 100 .
9 (50%) . 143-144 ºC. 141-143 ºC.()
, ν, -1 : 1595 (=N), 1357, 1537 (NO2)
-4--2--1,3-
3,62 (0,02 ) 4-[2,1,3]-1- 20 2.36 (0,04 ) . 1 20 . . 300 (350). MgSO4. , . : = 1:3. 0,33 2,2,--4--2--1,3- 1,1 . 72%.
. . 136-138 .. , ν, -1 : 1595 (=N), 1357, 1537 (NO2) , λ ., . (lg ε): 254 (3.90), 547 (3.80). 1 (DCl3), δ, . .: 1.68 c (6, 23), 6.84 6.95 (1, ), 7.29 (1, , J=7.4 ). 7.40 (1, , J=9.4 ). 13, δ, . .: 24.40 (3), 99.01 (2), 120.20, 126.80, 127.87 ( ), 127.09, 137.16, 140.14 ( ).
2,2,--4--2--1,3-
0.5 2,2,--4--2--1,3- 5 . 133 ºC , 5 . 15 8--3H--[]-[1,2,5]- 4-. . . : = 1:3. 63% 8--3H--[]-[1,2,5]--4-. 8--3,3--3-[1,2,5]-4- (63 %) . . .-. 55-57.. , ν, -1 : 1344, 1529 (-NO2). , λ ., . (lg ε): 404(3.30). 1 (CDCl3), δ, . .: 1.59 c (6, 23), 6.78 (1, ), 7.38 (1, ).7.53 (1, ). 13, δ, . .: 19.90 (23),95.95 (2), 123.91, 124.44, 128.31 ( ), 129.37, 143.18, 143.80, ( ).
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8--3H--[]-[1,2,5]--4-
100 8--3H--[]-[1,2,5]--4- , . 2,2,--4--2--1,3-.
- 2,2,--4--2--1,3-. 8--3H--[]-[1,2,5]--4-, 2,2,--4--2--1,3-.
3. 8--3H--[]-[1,2,5]--4- , . - .
1. Boiani M., Boiani L., Denicola A., Torres de Ortiz S., Serna E., Bilbao N.V., Sanabria L., Yaluff G., Nakayama H., Arias A.R., Vega C., Rolan M., Gomez-Barrio A., Cerecetto H., Gonzalez M.. 2-Benzimidazole 1,3-Dioxide Derivatives: A New Family of Water-Soluble Anti-Trypanosomatid Agents. // J. Med. Chem. 2006. V.49. P. 3215-3224.
2. Aguirre G., Boiani M., Cerecetto H., Gerpe A., Gonzalez M., Sainz Y. F., Denicola A., Ocariz Carmen Ochoa de, Nogal J.J., Montero D., Escario J. A. Novel Antiprotozoal Products: Imidazole and Benzimidazole N-Oxide Derivatives and Relater Compounds. // Arch. Pharm. Pharm. Med. Chem. 2004. V. 337. P. 259-270.
3. Part of this research is presented in the Uruguayan patent of invention: Boiani M., Cerecetto H., Gonzalez M., Merlino A. Derivados de 1,3-dioxido de benzimidazol. Procedimiento de preparacion y utilizacion (Benzimidazole 1,3-dioxide derivatives. Preparation procedure and utilization). UR Patent No. 29076, 2005.
4. Volkamer K., Zimmermann H.W. Uber arylsubstituierte 1-Hydroxy-imidazole und 1-Hydroxy-imidazol-N-3-oxide. // Chem. Ber. - 1969. - Bd.102. N.12. - S. 4177-4187.
5. Marwan J. Abu El-Haj. Novel Synthesis of 1-Hydroxy-1H-benzimidazole 3- Oxides and 2,2-Dialkyl-2H-benzimidazole 1,3-Dioxides. // J. Org. Chem. 1972. V. 37. P. 2519-2520.
6. Latham D.W.S., Meth-Cohn O., Suschitzky H., Herbert J.A.L. Benzofurazan N-Oxides as Synthetic Precursors. Part 2. Conversion of Benzofurazan N-Oxides into 2H-Benzimidazoles and Some Unusual Reachtions of 2H-Benzimidazoles. // J. Chem. Soc. Perkin. Trans. 1. - 1977. N.5. P. 470-478.
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7. Bulacinski A.B., Screven E.F.V., Suschitzky H. The reaction of benzofuroxan with p-anisylazide: trapping of the o-dinitrosointermediate. // Tetrahedron Lett. - 1975. N.41. P.3577-3578.
8. Garner G.V., Suschitzky H. The thermal uncatalysed cyclisation of N-cyclohexyl-o-nitroaniline: the question of a nitrene versus an aci-nitro mechanism. // Tetrahedron Lett. - 1971. N.2. P. 169-172.
9. Dirlam J.P., Cue B.W., Combatz K.J. Thermal decomposition of 2-azidoquinoxaline N-oxides. // J.Org. Chem. - 1978. V.43. N.1. P.76-79.
10. .., .. N- 4,7--2- . // . . . - 1982. .18. .3. c. 656-662.
11. .., .., .. 2--1,3- . - 1994. -N.4. .524-528.
12. .. . 2008.
13. Mallory. F. B. Varimbi S. P. J. org. chem. 1963. v28. p. 1656-1662.
14. . . . . . . . 1983 . . 227.
15. Samsonov V.A., Gatilov Yu. V., Savel'ev, V. A, Russian journal of organic chemistry, 2013, Vol. 49, No. 8, pp. 1223 − 1229.
