Abstract
Chiral 1H-pyrazolo[3,4-b]pyridines fused with nopinane frame were obtained by FeCl3-catalyzed assembling of pinocarvone oxime and 1-aryl-1H-pyrazol-5-amines. Chemical structures of new compounds were solved by NMR spectroscopy and confirmed by quantum chemical calculations and X-ray crystallography.
References
1.
von Zelewsky A., Mamula O.
Journal of the Chemical Society Dalton Transactions,
2000
2.
Chelucci G., Thummel R.P.
Chemical Reviews,
2002
3.
Kendre D.B., Toche R.B., Jachak M.N.
Tetrahedron,
2007
4.
Ghotekar B.K., Kazi M.A., Jachak M.N., Toche R.B.
Canadian Journal of Chemistry,
2008
5.
Yao C., Lu K., Song B., Liu B., Li T., Yu C.
Journal of Heterocyclic Chemistry,
2014
6.
Deore R., Dingore K., Jachak M.
Journal of Fluorescence,
2015
7.
Chen J., Liu W., Ma J., Xu H., Wu J., Tang X., Fan Z., Wang P.
Journal of Organic Chemistry,
2012
8.
Chen J., Liu W., Wang Y., Zhang H., Wu J., Xu H., Ju W., Wang P.
Tetrahedron Letters,
2013
9.
Wu H., Lian S., Shen Y., Wan Y.
Analytical Sciences,
2007
10.
Patil S.R., Shelar D.P., Rote R.V., Jachak M.N.
Journal of Fluorescence,
2011
11.
10.1016/j.mencom.2018.11.006_bibe0060
Dubey
Asian J. Chem.,
2002
12.
Costantino L., Barlocco D.
Current Medicinal Chemistry,
2005
13.
Duarte C., Barreiro E., Fraga C.
Mini-Reviews in Medicinal Chemistry,
2007
14.
Meiners B.A., Salama A.I.
European Journal of Pharmacology,
1982
15.
Revesz L., Blum E., Di Padova F.E., Buhl T., Feifel R., Gram H., Hiestand P., Manning U., Neumann U., Rucklin G.
Bioorganic and Medicinal Chemistry Letters,
2006
16.
Manetti F., Schenone S., Bondavalli F., Brullo C., Bruno O., Ranise A., Mosti L., Menozzi G., Fossa P., Trincavelli M.L., Martini C., Martinelli A., Tintori C., Botta M.
Journal of Medicinal Chemistry,
2005
17.
Witherington J., Bordas V., Gaiba A., Garton N.S., Naylor A., Rawlings A.D., Slingsby B.P., Smith D.G., Takle A.K., Ward R.W.
Bioorganic and Medicinal Chemistry Letters,
2003
18.
Wenglowsky S., Ren L., Ahrendt K.A., Laird E.R., Aliagas I., Alicke B., Buckmelter A.J., Choo E.F., Dinkel V., Feng B., Gloor S.L., Gould S.E., Gross S., Gunzner-Toste J., Hansen J.D., et. al.
ACS Medicinal Chemistry Letters,
2011
19.
Chibiryaev A.M., De Kimpe N., Tkachev A.V.
Tetrahedron Letters,
2000
20.
Vasilyev E.S., Agafontsev A.M., Tkachev A.V.
Synthetic Communications,
2014
21.
Vasilyev E.S., Bagryanskaya I.Y., Tkachev A.V.
Mendeleev Communications,
2017
22.
Allais C., Grassot J., Rodriguez J., Constantieux T.
Chemical Reviews,
2014
23.
Gallaher K.L., Lukco D., Grasselli J.G.
Canadian Journal of Chemistry,
1985
24.
Moir J.
Journal of the Chemical Society Transactions,
1902
25.
Ganesan A., Heathcock C.H.
Journal of Organic Chemistry,
1993
26.
Volochnyuk D.M., Ryabukhin S.V., Plaskon A.S., Dmytriv Y.V., Grygorenko O.O., Mykhailiuk P.K., Krotko D.G., Pushechnikov A., Tolmachev A.A.
Journal of Combinatorial Chemistry,
2010
27.
10.1016/j.mencom.2018.11.006_bibe0140
Tkachev
Ross. Khim. Zh. (Zh. Ross. Khim. Ob-va im. D. I. Mendeleeva),
1998
28.
Petukhov P.A., Bizyaev S.N., Tkachev À.V.
Russian Chemical Bulletin,
2001
29.
SHI F., ZHANG Y., TU S., ZHOU D., LI C., SHAO Q., CAO L.
Chinese Journal of Chemistry,
2008
30.
Zhu S., Ji S., Zhao K., Liu Y.
Tetrahedron Letters,
2008
31.
Wang S., Ma N., Zhang G., Shi F., Jiang B., Lu H., Gao Y., Tu S.
Journal of Heterocyclic Chemistry,
2010
32.
Jiang B., Liu Y., Tu S.
European Journal of Organic Chemistry,
2011
33.
34.
Lidström P., Tierney J., Wathey B., Westman J.
Tetrahedron,
2001
35.
Neese F.
Wiley Interdisciplinary Reviews: Computational Molecular Science,
2011
36.
Toomsalu E., Burk P.
Journal of Molecular Modeling,
2015
37.
Foresman J.B., Keith T.A., Wiberg K.B., Snoonian J., Frisch M.J.
The Journal of Physical Chemistry,
1996
38.
Aidas K., Angeli C., Bak K.L., Bakken V., Bast R., Boman L., Christiansen O., Cimiraglia R., Coriani S., Dahle P., Dalskov E.K., Ekström U., Enevoldsen T., Eriksen J.J., Ettenhuber P., et. al.
Wiley Interdisciplinary Reviews: Computational Molecular Science,
2013
39.
APEX2, Version 2.0, SAINT, Version 8.18c and SADABS, Version 2.11, Bruker Advanced X-ray Solutions, Bruker AXS, Madison, WI, USA, 2000-2012.
40.
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography,
2007
41.
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography,
2009
42.
M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka and M. A. Spackman, CrystalExplorer17, University of Western Australia, 2017, http://hirshfeldsurface.net.
43.
Jayatilaka D., Grimwood D.J.
Lecture Notes in Computer Science,
2003
44.
Turner M.J., Grabowsky S., Jayatilaka D., Spackman M.A.
Journal of Physical Chemistry Letters,
2014
45.
Padalkar V.S., Patil V.S., Phatangare K.R., Umape P.G., Sekar N.
Synthetic Communications,
2011