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16_potopnyk

Ser. Khim. 2008. No 49. Part 2. P. 96–101 O (&)
Ph-NH-NH2
1) KOH, EtOH
8, X = S, Y = O;
9, X = O, Y = S
10, X = S, Y = O;
11, X = O, Y = S
10, 11 13,
18–21. +
R = COOEt (14,18); C(S)NH2 (15,19); CONHPh (16,20);
! 2-(* !+,( $
5+4 1H, ': 1,33 (3 H, CH3,.2, J = 6,8); 2,06 (3 ., CH3); 4,20 (2 ., ,.2), J = 6,8); 6,84 (1 H, Ph); 7,19–7,28 (4 H, Ph); 9,65 (1 H, , %: C 63,77; H 6,32; N 13,12. C11H14N2O2. ) ! 4-* (% !-1-* !-1H- ( $ !-3-
5+4 1H, ': 1,42 (3 H, CH3,.2, J = 7,2); 4,42 (2 H, CH2), J = 7,2); 7,40 (1 H, Ph, J = 7,6); 7,51 (2 H, Ph, J = 7,6); 7,98 (2 H, Ph, J = 7,6); 9,17 , %: C 63,27; H 4,84; N 11,02. C13H12N2O3. (% !-1-* !-1H- ( $ !-3-
5+4 1., ': 7,41 (1 ., Ph, J = 8,0); 7,53 (2 ., Ph, J = 8,0); 8,00 (2 ., Ph, J = 8,0); 9,14 (1 ., $ ! 4-[(1,3-R2-2,4,6- (
" ( +,( -5(2H)-
% !]-1-* !-1 - ( $ !-3-
& (6, 7).
4-[(2,4,6- (
" ( +,( -5(2H)-
! , )% !]-1-* !-
1 - ( $!-3- (# " ! (6).
(2 H, CH2)); 7,48 (1 H, Ph); 7,60 (2 H, Ph); 7,85 (2 H, Ph); 8,96 (1 H, 9,67 (1 H, CH=); 11,31 (1 ., NH); 11,37 (1 ., NH). ! ! 4-[(1,3-, % !-2,4,6- (
" ( +,( -5(2H)-
!]-1-* !-1 - ( $ !-3-
(2), 0,32 (2,0
5+4 1H, ': 1,41 (3 H, CH3,.2); 3,12 (6 ., 2CH3N); 4,41 (2 H, CH2)); 7,49 (1 H, Ph); 7,60 (2 H, Ph); 7,83 (2 H, Ph); 9,01 (1 H, , %: C 58,91; H 4,55; N 14,32. C19H18N4O5. ) 4-[(4(2)- " -2(4)-
" -1,3-
$ ! , -5- ! , )% !]-1-* !-1 -
(10, 11). ,
4-[(4- " -2-
" -1,3-
$ ! , -5- ! , )% !]-1-* !-1 - ( -
(10). * . = 235 °,.
4-[(2- " -4-
" -1,3-
$ ! , -5- ! , )% !]-1-* !-1 - ( -
(11). * . = 238 °,.
CH3,.2); 4,34 (2 H, CH2)); 7,41 (1 H, Ph); 7,52 (2 H, Ph); 7,92 (2 H, Ph); 8,01 ! 4-[(3-% !-5-
" -1-* !-1,5-, +,( -4 - ( $ !-4- ! , )% !]-1-
* !-1 - ( $ !-3-
(2), 0,7 (4,1
, %: C 68,17; H 4,82; N 13,55. C23H20N4O3. ) 18–21.
14–17 8
-3- " -3- " -1- ( !)-1-* !-1 - ( $!-3- (# -
(18). * . = 126–128 °, (
CH3,.2); 1,43 (3 H, CH3,.2); 4,34 (2 H, CH2)); 4,41 (2 H, CH2)); 7,47 (1 H, Ph); 7,58 (2 H, Ph); 7,89 (2 H, Ph); 8,86 (1 H, CH=); 9,14 (1 H, -3- " -1- ( !)-1-* !-1 - ( $!-3- (# -
(19). * . = 188–190 °, (
1,43 (3 H, CH3,.2, J = 7,2); 4,43 (2 H, CH2), J = 7,2); 7,11 (1 H, Ph, J = 7,6); 7,33 (2 H, Ph, J = 7,6); 7,47 (1 H, Ph, J = 7,6); 7,60 (2 H, Ph, J = 7,6); 7,70 (2 H, Ph, J = 7,6); 7,92 (2 H, Ph, J = 7,6); 8,75 (1 H, CH=); 9,15 (1 H, , %: C 67,21; H 4,63; N 14,05. C22H18N4O3. ) 4-(3- % -2--
" -1- ( !)-1-* !-1 - ( $ !-3-
(20). * . = 264–265 °, ( +60).
(3 H, CH3,.2, J = 7,2); 4,41 (2 H, CH2), J = 7,2); 7,46 (1 H, Ph, J = 7,6); 7,59 (2 H, Ph, J = 7,6); 7,89 (2 H, Ph, J = 7,6); 8,70 (1 H, CH=); 9,16 (1 H, -2-(4-* !-1,3- $!-2- !) !]-1-* !-1 - ( $!-3- (-
(21). * . = 196 °, ( +60).
CH3,.2, J = 7,2); 4,45 (2 H, CH2), J = 7,2); 7,36 (1 ., Ph); 7,45 (3 ., Ph); 7,60 (2 ., Ph); 7,93 (2 ., Ph); 8,01 (2 ., Ph); 8,12 (1 ., , %: C 66,84; H 4,03; N 12,86, S 7,42. C24H18N4O2S. ) $ 2-* !-2,6-, +,( -7H- ( $ ! [3,4-d]
2, 18–21 7
5+4 1.: 7,47 (1 ., Ph, J = 7,6); 7,58 (2 H, Ph, J = 7,6); 8,03 (2 ., Ph, J = 7,6); 8,26 c 1. Bebernitz G.R., Argentieri G., Battle B., Brennan C., Balkan B., Burkey B.F. et al. The Effect of 1.3-Diaryl-[1H]-pyrazole-4-acetamides on Glucose Utilization in ob/ob Mice // J. Med. Chem. 2001. Vol. 44. N 16. P. 2601–2611. 2. Abadi A.H., Eissa A.A.H., Hassan G.S. Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents // Chem. Pharm. 3. Lange J.H.M., van Stuivenberg H.H., Coolen H.K.A.C., Adolfs T.J.P. et al. Bioisosteric replacements of the pyrazole moiety of rimonabant: synthesis, biological properties, and molecular modeling investigations of thiazoles, triazoles, and imidazoles as potent and selective CB1 cannabinoid receptor antagonists // J. Med. Chem. 2005. Vol. 48. N 6. 4. Mallegol T., Gmouh S., Meziane M.A.A., Blanchard-Desce M., Mongin O. Practical and Efficient Synthesis of Tris(4-formylphenyl)amine, a Key Building Block in Materials Chemistry // Synthesis. 2005. N 11. 4. 1771–1774. 5. Caluwe P. Heteroannelations with o-aminoaldehydes // Tetrahedron. 1980. Vol. 36. 6. Denison S., Hilton S.T. A Convenient Synthesis of 2-Cyano-3-Substituted Indoles // Synlett. 2004. N 15. P 2806–2808.07.12.204 7. Kira M.A., Abdel-Raemann M.O., Gadalla K.Z. The Vilsmeier–Haack reaction.
III. Cyclization of hydrazones to hyrazoles // Tetrahedron Lett. 1969. N 2. P. 109–110. 8. Kira M.A., Aboul-Enein N.M., Korkor K.Z. The Vilsmeier–Haack reaction. IV. Reaction
of Phosphorus Oxychloride-Dimethylformamide with Semicarbazones // J. Heterocycl. 9. Brehme R., Gründemann E., Schneider M. Reaktion von Acetophenonmono-methyl- und -dimethylhydrazonen mit dem Vilsmeier–Reagenz; Bildung von Pyrazol-4-
carbiminiumsalzen: ein Beitrag zum Mechanismus // J. Prakt. Chem. 2000. Bd. 7. SYNTHESIS AND CHEMICALS CHARACTERISTICS OF ETHYL
4-FORMYL-1-PHENYL-1H-PYRAZOLE-3-CARBOXYLATE
M. Potopnyk, V. Matiychuk
Ivan Franko National University of Lviv, Kyryla & Mefodiya Str., 6, 79005 Lviv, Ukraine Ethyl 4-formyl-1-phenyl-1H-pyrazole-3-carboxylate was synthesized by reaction of ethyl 2-(phenylhydrazono)propanoate with the Vilsmeier–Haack complex. New methods of synthesis of 2-phenil-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-one were suggested. Key words: pyrazoles, Vilsmeier–Haack reagent.

Source: http://chem.lnu.edu.ua/visnyk_2008/ORGAN/16_Potopnyk.pdf