The preparation of 1-(β-naphthyl)-3-ferrocenylpyrazole-4-carbaldehyde and syntheses on the base of it
Abstract
Synthesis of 1-(β-naphthyl)-3-ferrocenyl pyrazole-4-carbaldehyde was carried out from acetylferrocene and naphthalen-2-ylhydrazine followed by intramolecular cyclization under Vilsmeier-Haack conditions. The reaction of reductive amination of aldehydes obtained with primary and secondary amines including methyl esters of amino acids was studied.
Keywords
547.57, 547.7
About the Authors
E. Yu. Osipova
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation
Russian Federation
A. A. Simenel
Институт элементоорганических соединений им. А.Н. Несмеянова РАН
Russian Federation
Russian Federation
A. N. Rodionov
Институт элементоорганических соединений им. А.Н. Несмеянова РАН
Russian Federation
Russian Federation
V. V. Kachala
Институт органической химии им. Н.Д. Зелинского РАН
Russian Federation
Russian Federation
K. Ya. Zherebker
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation
Russian Federation
References
1. Katritzky, A. R. Comprehensive heterocyclic chemistry / A. R. Katritzky. - Pergamon Press Ltd, 1984. - Vol. 5, part 4A. - 994 p.
2. Synthesis, structure characterization and preliminary biological evaluation of novel 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives Y. S. Xie [et al.] // J. Organomet. Chem. - 2008. - Vol. 693. - P. 1367-1374 .
3. Ferrocenylalkyl azoles: bioactivity, synthesis, structure / L. V. Snegur, Yu. S. Nekrasov, N. S. Sergeeva, Zh. V. Zhilina, V. V Gumenyuk, Z. A. Starikova, A. A. Simenel, N. B. Morozova, I. K. Sviridova, V. N. Babin // Appl. Organomet. Chem. - 2008. - Vol. 22. - P. 139-147.
4. Some new aspects of asymmetric catalysis with chiral ferrocenyl ligands / A. Togni, R. Dorta, C. Kollner, G. Pioda // Pure and Appl. Chem. - 1998. - Vol. 70, № 8. - P. 1477-1485.
5. 4-Functionally substituted 3-heterylpyrazoles: XVIII. Intramolecular cyclization of N-[3-(2-chlorophenyl)-4-pyrazolyl]methylamine and its N-alkyl derivatives into 4,5-dihydro-2H-pyrazolo[4,3- c]quinolines M. K. Bratenko, O. I. Panimarchuk, V. A. Chornous, M. V. Vovk // Russ. J. Org. Chem. - 2007. - Vol. 43, № 48. - P. 1209-1213.
6. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures / A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah // J. Org. Chem. - 1996. - Vol. 61. - P. 3849-3862.
7. Felleher, F. Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines F. Felleher, S. Kelly, V. McKee // Tetrahedron. - 2007. - Vol. 63. - P. 9235- 9242.
8. Portoghese, P. S. Design of peptidomimetic and opioid receptor antagonists using the message-address concept / P. S. Portoghese, M. Sultana, A.E. Takemori // J. Med. Chem. - 1990. - Vol. 33, № 6. - P. 1714-1720.
Review
For citations:
Osipova E.Yu., Simenel A.A., Rodionov A.N., Kachala V.V., Zherebker K.Y. The preparation of 1-(β-naphthyl)-3-ferrocenylpyrazole-4-carbaldehyde and syntheses on the base of it. Fine Chemical Technologies. 2009;4(2):100-105. (In Russ.)
Views: 275
Email this article 
