Home / Publications / Synthesis of novel highly functionalized triazole-linked calix[4]resorcinols via click reaction

Synthesis of novel highly functionalized triazole-linked calix[4]resorcinols via click reaction

Irina Rafaelevna Mironova (Knyazeva) 1
Irina Rafaelevna Mironova (Knyazeva)
, 
Dilara K Abdrafikova 2
Dilara K Abdrafikova
, 
Karina M Mukhamedyanova 2
Karina M Mukhamedyanova
, 
Victor Vasil'evich Syakaev 1
Victor Vasil'evich Syakaev
, 
Bulat Makhmudovich Gabidullin 1
Bulat Makhmudovich Gabidullin
, 
Aidar Timergalievich Gubaidullin 1
Aidar Timergalievich Gubaidullin
, 
Wolf D Habicher 3
Wolf D Habicher
, 
Alexander Romanovich Burilov 1
Alexander Romanovich Burilov
, 
Michael Arkad'evich Pudovik 1
Michael Arkad'evich Pudovik
10.1016/j.mencom.2017.11.005
Published 2017-10-30
Communication , Volume 27, Issue 6, 556-558
13
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Mironova (Knyazeva) I. R. et al. Synthesis of novel highly functionalized triazole-linked calix[4]resorcinols via click reaction // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 556-558.
GOST all authors (up to 50) Copy
Mironova (Knyazeva) I. R., Abdrafikova D. K., Mukhamedyanova K. M., Syakaev V. V., Gabidullin B. M., Gubaidullin A. T., Habicher W. D., Burilov A. R., Pudovik M. A. Synthesis of novel highly functionalized triazole-linked calix[4]resorcinols via click reaction // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 556-558.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2017.11.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.005
TI - Synthesis of novel highly functionalized triazole-linked calix[4]resorcinols via click reaction
T2 - Mendeleev Communications
AU - Mironova (Knyazeva), Irina Rafaelevna
AU - Abdrafikova, Dilara K
AU - Mukhamedyanova, Karina M
AU - Syakaev, Victor Vasil'evich
AU - Gabidullin, Bulat Makhmudovich
AU - Gubaidullin, Aidar Timergalievich
AU - Habicher, Wolf D
AU - Burilov, Alexander Romanovich
AU - Pudovik, Michael Arkad'evich
PY - 2017
DA - 2017/10/30
PB - Mendeleev Communications
SP - 556-558
IS - 6
VL - 27
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Mironova (Knyazeva),
author = {Irina Rafaelevna Mironova (Knyazeva) and Dilara K Abdrafikova and Karina M Mukhamedyanova and Victor Vasil'evich Syakaev and Bulat Makhmudovich Gabidullin and Aidar Timergalievich Gubaidullin and Wolf D Habicher and Alexander Romanovich Burilov and Michael Arkad'evich Pudovik},
title = {Synthesis of novel highly functionalized triazole-linked calix[4]resorcinols via click reaction},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.005},
number = {6},
pages = {556--558},
doi = {10.1016/j.mencom.2017.11.005}
}
MLA
Cite this
MLA Copy
Mironova (Knyazeva), Irina Rafaelevna, et al. “Synthesis of novel highly functionalized triazole-linked calix[4]resorcinols via click reaction.” Mendeleev Communications, vol. 27, no. 6, Oct. 2017, pp. 556-558. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.005.

Abstract

A single-step acid-catalyzed condensation of resorcinol or 2-methylresorcinol with 4-(prop-2-yn-1-yloxy)benzaldehyde stereoselectively gives exclusively rctt-isomers of new calix[4]- resorcinols in chair conformation bearing four terminal alkyne groups at aromatic substituents. Further alkylation of free hydroxy groups with propargyl bromide affords new calix[4]- resorcinols containing 12 terminal alkyne groups. Subsequent click reaction of these compounds with benzyl azide results in highly functionalized calix[4]resorcinols with 12 triazole- linked branches.

References

1.
Click To Bind: Metal Sensors
Bryant J.J., Bunz U.H.
Chemistry - An Asian Journal, 2013
2.
Recent advances in click chemistry reactions mediated by transition metal based systems
Tăbăcaru A., Furdui B., Ghinea I.O., Cârâc G., Dinică R.M.
Inorganica Chimica Acta, 2017
3.
Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends
Wang C., Ikhlef D., Kahlal S., Saillard J., Astruc D.
Coordination Chemistry Reviews, 2016
4.
Burilov V.A., Nugmanov R.I., Ibragimova R.R., Solovieva S.E., Antipin I.S.
Mendeleev Communications, 2015
6.
Synthesis of Calixarene-Based Cavitands and Nanotubes by Click Chemistry
Morales-Sanfrutos J., Ortega-Muñoz M., Lopez-Jaramillo J., Hernandez-Mateo F., Santoyo-Gonzalez F.
Journal of Organic Chemistry, 2008
7.
Synthesis of lactosylated glycoclusters and inhibition studies with plant and human lectins
Cecioni S., Matthews S.E., Blanchard H., Praly J., Imberty A., Vidal S.
Carbohydrate Research, 2012
8.
Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands
Bernardi S., Fezzardi P., Rispoli G., Sestito S.E., Peri F., Sansone F., Casnati A.
Beilstein Journal of Organic Chemistry, 2014
12.
Calixarene-Based Chemosensors by Means of Click Chemistry
Song M., Sun Z., Han C., Tian D., Li H., Kim J.S.
Chemistry - An Asian Journal, 2014
13.
Click synthesis of triazole-linked calix[4]arene ionophores. Potentiometric and ESI-MS screening of ion-selectivity
Czirok J.B., Jágerszki G., Tóth K., Révész Á., Drahos L., Bitter I.
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2013
16.
Novel analogs of antitumor agent calixarene 0118: Synthesis, cytotoxicity, click labeling with 2-[18F]fluoroethylazide, and in vivo evaluation
Läppchen T., Dings R.P., Rossin R., Simon J.F., Visser T.J., Bakker M., Walhe P., van Mourik T., Donato K., van Beijnum J.R., Griffioen A.W., Lub J., Robillard M.S., Mayo K.H., Grüll H., et. al.
European Journal of Medicinal Chemistry, 2015
17.
Design, synthesis, and drug solubilising properties of the first folate–calix[4]arene conjugate
Consoli G.M., Granata G., Geraci C.
Organic and Biomolecular Chemistry, 2011
19.
Host-guest complexation. 48. Octol building blocks for cavitands and carcerands
Tunstad L.M., Tucker J.A., Dalcanale E., Weiser J., Bryant J.A., Sherman J.C., Helgeson R.C., Knobler C.B., Cram D.J.
Journal of Organic Chemistry, 1989
20.
Self-Assembled Monolayers of Receptor Adsorbates on Gold: Preparation and Characterization
Thoden van Velzen E.U., Engbersen J.F., Reinhoudt D.N.
Journal of the American Chemical Society, 1994
22.
Rapid synthesis of dendrimers based on calix[4]resorcinarenes
Yamakawa Y., Ueda M., Nagahata R., Takeuchi K., Asai M.
Journal of the Chemical Society Perkin Transactions 1, 1998
24.
One-step synthesis of rccc- and rctt-diastereomers of novel calix[4]resorcinols based on a para-thiophosphorylated derivative of benzaldehyde
Knyazeva I.R., Sokolova V.I., Gruner M., Habicher W.D., Syakaev V.V., Khrizanforova V.V., Gabidullin B.M., Gubaidullin A.T., Budnikova Y.H., Burilov A.R., Pudovik M.A.
Tetrahedron Letters, 2013
25.
Thiophosphorylated derivatives of meta- and ortho-hydroxybenzaldehydes in one-step syntheses of novel calix[4]resorcinols
Knyazeva I.R., Matveeva V.I., Syakaev V.V., Gabidullin B.M., Gubaidullin A.T., Gruner M., Habicher W.D., Burilov A.R., Pudovik M.A.
Tetrahedron Letters, 2014
26.
Phosphorus-containing calix[4]resorcinols: Synthesis and properties
Knyazeva I.R., Burilov A.R., Pudovik M.A., Sinyashin O.G.
Phosphorus, Sulfur and Silicon and the Related Elements, 2016