Semicarbazone Derivatives
323
1993, 35, 539; (b) Guzman, A.; Ronero, M.; Maddox, M. L.; Machowski, J.
M. Vilsmeier–Haack reaction with glutarimides: Synthesis of 2,6-dichloro-
1,4-dihydropyridine-3,5-dicarboxaldehydes. J. Org. chem. 1990, 55, 5793; (c)
Mahatta, P. K.; Venktash, C.; Shyam kumar, U. K.; Ila, H.; Junjappa, H.
Reaction of -oxoketene-n,s-arylaminoacetals with Vilsmeier reagents: An effi-
cient route to highly functionalized quinolines and their benzo=hetero-fused
analogues. J. Org. Chem. 2003, 68, 3966; (d) Katrizky, A. R.; Arend, M. A.
Convenient and highly regioselective one-pot synthesis of quinolines by addi-
tion of a Vilsmeier-type reagent to n-arylimines. J. Org. Chem. 1998, 63, 9989.
3. Kira, M. A.; Abdel-Rahman, M. O.; Gadalla, K. Z. The Vilsmeier–Haack
reaction III: Cyclization of hydrazones to pyrazoles. Tetrahedron Lett.
1969, 10, 109.
4. (a) Dimmock, J. R.; Puthucode, R. N.; Smith, J. M.; Hetherington, M.;
Quail, J.W.; Pugazhenthi, U.; Lechler, T.; Stables, J. P. (Aryloxy)aryl semi-
carbazones and related compounds: A novel class of anticonvulsant agents
possessing high activity in the maximal electroshock screen. J. Med. Chem.
1996, 39, 3984; (b) Dimmock, J. R.; Vashishtha, S. C.; Stables, J. P. Anti-
convulsant properties of various acetylhydrazones, oxamoylhydrazones,
and semicarbazones derived from aromatic and unsaturated carbonyl com-
pounds. Eur J. Med. Chem. 2000, 35, 241; (c) Yogeeswari, P.; Sriram, D.;
Thirumurugan, R.; Reghavendran, J. V.; Sudhan, K.; Kumar, R. P.; Stables,
J. Discovery of N-(2,6-dimethylphenyl)-substituted semicarbazones as antic-
onvulsants: Hybrid pharmacophore-based design. J. Med. Chem. 2005, 48,
6202; (d) Yogeeswari, P.; Sriram, D.; Saxena, A.; Thirumurugan, R.; Stables,
J. 2,4-Dimethoxyphenylsemicarbazones with anticonvulsant activity against
three animal models of seizures: Synthesis and pharmacological evaluation.
Biorg. Med. Chem. 2006, 14, 3106; (e) Yogeeswari, P.; Thirumurugan, R.;
Sriram, D.; Suniljit, L. R. J.; Reghavendran, J. V.; Kavya, R.; Rakhera,
K.; Stables, J. Synthesis of N4-(2,4-dimethylphenyl) semicarbazones as
4-aminobutyrate aminotransferase inhibitors. Acta Pharm. 2006, 56, 259.
(f) Berlado, H.; Gambino, D. The wide pharmacological versatility of semi-
carbazones, thiosemicarbazones, and their metal complexes. Mini-Rev.
Med. Chem. 2004, 4(1), 31.
5. Bal, T.; Atasever, B.; Solakoglu, Z.; Kuruca, S. E.; Wkiiseven, B. Synthesis,
characterization, and cytotoxic properties of the N1,N4-diarylidene-S-methyl-
thiosemicarbazone chelates with Fe(III) and Ni(II). Eur. J. Med. Chem. 2007,
42, 161.
6. (a) Prakash, O.; Kumar, R.; Bhardwaz, V.; Sharma, P. K. Synthesis of some
new 3-aryl-4-formyl-1-(4,6-dimethyl-2-pyrimidinyl)pyrazoles using Vilsmeier–
Haack reaction. Hetcrocycl. Commun. 2003, 9(5), 515; (b) Kumar, A.;
Prakash, O.; Kinger, M.; Singh, S. P. Synthesis of some new 1-aryl-4-
formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the
Vilsmeier–Haack reaction—Isolation of the key intermediate 1-aryl-3-(4-
hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles.Can.J.Chem.2006,84,438.
7. (a) Loncle, C.; Brunel, J. M.; Vidal, N.; Dherbomez, M.; Letourneux, Y.
Synthesis and antifungal activity of cholesterol-hydrazone derivatives. Eur.