Azide–Akyne Click Approach to the Preparation of Dendrimer–Type Multi(thia)calix[4]arenes with Triazole Linkers

Anton A. Muravev,^a@ Alexei I. Laishevtsev,^b Farida B. Galieva,^b Ol’ga B. Bazanova,^a Il’dar Kh. Rizvanov,^a Ali Korany,^c Svetlana E. Solovieva,^a,b Igor S. Antipin,^a,b and Alexander I. Konovalov^a

^aA.E. Arbuzov Institute of Organic and Physical Chemistry, 420088 Kazan, Russia

^bKazan Federal University, 420111 Kazan, Russia

^cDepartment of Applied Organic Chemistry, National Research Center, 12622 Dokki-Cairo, Egypt

^@Corresponding author E-mail: antonm@iopc.ru

DOI: 10.6060/mhc170304m

Macroheterocycles2017 10(2) 203-214

The design of polymacrocyclic structures is of high importance for the improvement of recognition ability to various guests. We present a convenient approach towards two types of dendrimer-shaped pentakis-thiacalix[4]arenes with triazolyl linkers using the click reaction of tetraazidoalkoxycalixarenes with monoalkynyloxy derivatives, as well as tetraalkynyloxycalixarenes with monoazidoalkoxy derivatives. Mitsunobu alkylation of hydroxyl groups has been employed to afford tetrasubstituted derivatives in 1,3-alternate configuration. A facile procedure for the synthesis of monosubstituted cone precursors in high yields by the hydrolysis of one ether fragment in disubstituted counterparts under basic conditions (n-BuNH₂ or NaN₃ in DMF) has been suggested and optimized. CuAAC reaction has been conducted in microwave reactor and on a hot plate. It has been found that microwave irradiation promotes the reaction and the yields of products are as high as 40–80 %.

References:

Click here to expand or collapse this section

1. a) Designing Dendrimers (Campagna S., Ceroni P., Puntoriero F., Eds.) Hoboken: Wiley, 2011. 616 p.;
b) Astruc D., Boisselier E., Ornelas C. Chem. Rev. 2010, 110, 1857–1959;
https://doi.org/10.1021/cr900327d
c) Dendrimers, Dendrons, and Dendritic Polymers (Tomalia D.A., Christensen J.B., Boas U., Eds.) Cambridge: Cambridge Univ. Press, 2012. 412 p.

2. a) Calixarenes. An Introduction (Gutsche C.D., Ed.) Cambridge: Royal Society of Chemistry, 2008. 276 p.;
b) Morohashi N., Narumi F., Iki N., Hattori T., Miyano S. Chem. Rev. 2006, 106, 5291–5316;
https://doi.org/10.1021/cr050565j
c) Konovalov A.I., Antipin I.S. Mendeleev Commun. 2008, 18, 229–237;
https://doi.org/10.1016/j.mencom.2008.09.001
d) Kumar R., Lee Y.O., Bhalla V., Kumar M., Kim J.S. Chem. Soc. Rev. 2014, 43, 4824–4870;
https://doi.org/10.1039/c4cs00068d
e) Muravev A.A., Burilov V.A., Solov'eva S.E., Strel'nik A.G., Latypov S.K., Bazanova O.B., Sharafutdinova D.R., Antipin I.S., Konovalov A.I. Russ. Chem. Bull. 2014, 63, 214.
https://doi.org/10.1007/s11172-014-0416-y

3. Rudzevich Y., Fischer K., Schmidt M., Böhmer V. Org. Biomol. Chem. 2005, 3, 3916–3925.
https://doi.org/10.1039/b509948j

4. Rotan O., Sokolova V., Gilles P., Hu W., Dutt S., Schrader T., Epple M. Mat.-wiss. u.Werkstofftech. 2013, 44, 176–182.
https://doi.org/10.1002/mawe.201300085

5. a) Lalor R., DiGesso J.L., Mueller A., Matthews S.E. Chem. Commun. 2007, 46, 4907–4909;
https://doi.org/10.1039/b712100h
b) Lu Y., Xiao C., Yu Z., Zeng X., Ren Y., Li C. J. Mater. Chem. 2009, 19, 8796–8802.
https://doi.org/10.1039/b913874a

6. a) Jiansen L., Zhenlin Z., Yuanyin C., Xueran L. Tetrahedron Lett. 1998, 39, 6507–6510;
https://doi.org/10.1016/S0040-4039(98)01353-7
b) Tilki T., Şener I., Karcı F., Gülce A., Deligöz H. Tetrahedron 2005, 61, 9624–9629;
https://doi.org/10.1016/j.tet.2005.07.078
c) Bhalla V., Nagendra Babu J., Kumar M., Hattori T., Miyano S. Tetrahedron Lett. 2007, 48, 1581–1585.
https://doi.org/10.1016/j.tetlet.2006.12.142

7. Hamdi A., Lee Y.H., Kim Y., Kusumahastuti D.K.A., Ohto K., Abidi R., Vicens J. Tetrahedron Lett. 2009, 50, 540–543.
https://doi.org/10.1016/j.tetlet.2008.11.068

8. a) Csokai V., Balázs B., Tóth G., Horváth G., Bitter I. Tetrahedron 2004, 60, 12059–12066;
https://doi.org/10.1016/j.tet.2004.10.037
b) Khomich E., Kashapov M., Vatsouro I., Shokova E., Kovalev V. Org. Biomol. Chem. 2006, 4, 1555–1560;
https://doi.org/10.1039/b601709f
c) Kim S.K., Sim W., Vicens J., Kim J.S. Tetrahedron Lett. 2003, 44, 805–809;
https://doi.org/10.1016/S0040-4039(02)02657-6
d) Muravev A.A., Galieva F.B., Bazanova O.B., Sharafutdinova D.R., Solovieva S.E., Antipin I.S., Konovalov A.I. Supramol. Chem. 2016, 28, 589–600.
https://doi.org/10.1080/10610278.2016.1150593

9. a) Pappalardo A., Ballistreri F.P., Li Destri G., Mineo P.G., Tomaselli G.A., Toscano R.M., Sfrazzetto G.T. Macromolecules 2012, 45, 7549–7556;
https://doi.org/10.1021/ma3015239
b) Wiktorowicz S., Aseyev V., Tenhu H. Polym. Chem. 2012, 3, 1126–1129;
https://doi.org/10.1039/c2py20020a
c) Prata J.V., Costa A.I., Pescitelli G., Pinto H.D. Polym. Chem. 2014, 5, 5793–5803.
https://doi.org/10.1039/C4PY00729H

10. a) Galán H., Teresa Murillo M., Quesada R., Escudero-Adán E.C., Benet-Buchholz J., Prados P., de Mendoza J. Chem. Commun. 2010, 46, 1044–1046;
https://doi.org/10.1039/B921465H
b) Feng J., Liu K., Li Y., Yang M. Polym. Adv. Technol. 2009, 20, 514–518;
https://doi.org/10.1002/pat.1374
c) Gattuso G., Grasso G., Marino N., Notti A., Pappalardo A., Pappalardo S., Parisi M.F. Eur. J. Org. Chem. 2011, 5696–5703;
https://doi.org/10.1002/ejoc.201100812
d) Lalor R., Gunning A.P., Morris V.J., Matthews S.E. Chem. Commun. 2010, 46, 8665–8667;
https://doi.org/10.1039/c0cc02784g
e) Bu J.-H., Zheng Q.-Y., Chen C.-F., Huang Z.-T. Tetrahedron 2005, 61, 897–902;
https://doi.org/10.1016/j.tet.2004.11.043
f) Wang J., Gutsche C.D. J. Org. Chem. 2002, 67, 4423–4429;
https://doi.org/10.1021/jo0110808
g) Szemes F., Drew M.G.B., Beer P.D. Chem. Commun. 2002, 1228–1229;
https://doi.org/10.1039/b202315f
h) Stastny V., Stibor I., Dvorakova H., Lhotak P. Tetrahedron 2004, 60, 3383–3391.
https://doi.org/10.1016/j.tet.2004.02.036

11. a) Fischer C., Weber E. J. Incl. Phenom. Macrocycl. Chem. 2014, 79, 151–160;
https://doi.org/10.1007/s10847-013-0338-6
b) Morales-Sanfrutos J., Ortega-Mu-oz M., Lopez-Jaramillo J., Hernandez-Mateo F., Santoyo-Gonzalez F. J. Org. Chem. 2008, 73, 7768–7771;
https://doi.org/10.1021/jo801325c
c) Hwang G.T., Kim B.H. Tetrahedron 2002, 58, 9019–9028.
https://doi.org/10.1016/S0040-4020(02)01125-0

12. a) Li H., Zhan J., Chen M., Tian D., Zou Z. J. Incl. Phenom Macrocycl Chem. 2010, 66, 43–47;
https://doi.org/10.1007/s10847-009-9582-1
b) Wang N.J., Sun C.M., Chung W.S. Sens. Actuators, B 2012, 171–172, 984–993;
https://doi.org/10.1016/j.snb.2012.06.014
c) Cecioni S., Lalor R., Blanchard B., Praly J.P., Imberty A., Matthews S.E., Vidal S. Chem. Eur. J. 2009, 15, 13232–13240.
https://doi.org/10.1002/chem.200901799

13. Armarego W.L.F. Purification of Laboratory Chemicals (Armarego W.L.F., Chai C.L.L., Eds.) Oxford: Butterworth-Heinemann, 2009. 760 p.

14. Tyuftin A.A., Solovieva S.E., Murav'ev A.A., Polyantsev F.M., Latypov Sh.K., Antipin I.S. Russ. Chem. Bull. 2009, 58, 145–151.
https://doi.org/10.1007/s11172-009-0022-6

15. a) Bitter I., Csokai V. Tetrahedron Lett. 2003, 44, 2261–2265
https://doi.org/10.1016/S0040-4039(03)00285-5;
b) Muravev A.A., Galieva F.B., Strel'nik A.G., Nugmanov R.I., Gruner M., Solov'eva S.E., Latypov Sh.K., Antipin I.S., Konovalov A.I. Russ. J. Org. Chem. 2015, 51, 1334–1342.
https://doi.org/10.1134/S1070428015090213

16. Solov'eva S.E., Murav'ev A.A., Latypov Sh.K., Antipin I.S., Konovalov A.I. Dokl. Chem. 2011, 438, 170–174.
https://doi.org/10.1134/S0012500811060061

17. Akdas H., Bringel L., Bulach V., Graf E., Hosseini M.W., De Cian A. Tetrahedron Lett. 2002, 43, 8975–8979.
https://doi.org/10.1016/S0040-4039(02)02152-4

18. Lang J., Vlach J., Dvorakova H., Lhotak P., Himl M., Harbal R., Stibor I. J. Chem. Soc., Perkin Trans. 2 2001, 576–580.
https://doi.org/10.1039/b007887p

19. Burilov V.A., Ibragimova R.R., Nugmanov R.I., Sitdikov R.R., Islamov D.R., Kataeva O.N., Solov'eva S.E., Antipin I.S. Russ. Chem. Bull. 2015, 64, 2114–2124.
https://doi.org/10.1007/s11172-015-1126-9

20. Burilov V.A., Nugmanov R.I., Ibragimova R.R., Solovieva S.E., Antipin I.S. Mendeleev Commun. 2015, 25, 177–179.
https://doi.org/10.1016/j.mencom.2015.05.005

21. Lavendomme R., Leroy A., Luhmer M., Jabin I. J. Org. Chem. 2014, 79, 6563−6570.
https://doi.org/10.1021/jo501021c

22. Lavendomme R., Zahim S., De Leener G., Inthasot A., Mattiuzzi A., Luhmer M., Reinaud O., Jabin I. Asian J. Org. Chem. 2015, 4, 710–722.
https://doi.org/10.1002/ajoc.201500178

23. Matsumiya H., Terazono Y., Iki N., Miyano S. J. Chem. Soc., Perkin Trans. 2 2002, 1166–1172.
https://doi.org/10.1039/b200228k

24. a) Omran O.A. Heterocycles 2016, 92, 1085;
https://doi.org/10.3987/COM-16-13458
b) Kasyan O., Healey E.R., Drapailo A., Zaworotko M., Cecillon S., Coleman A.W., Kalchenko V. J. Incl. Phenom. Macrocycl. Chem. 2007, 58, 127–132;
https://doi.org/10.1007/s10847-006-9134-x
c) Galukhin A.V., Zaikov E.N., Antipin I.S., Konovalov A.I., Stoikov I.I. Macroheterocycles 2012, 5, 266–274;
https://doi.org/10.6060/mhc2012.120781s
d) Stoikov I.I., Ibragimova D.S., Shestakova N.V., Krivolapov D.B., Litvinov I.A., Antipin I.S., Konovalov A.I., Zharov I. Supramol. Chem. 2009, 21, 564–571;
https://doi.org/10.1080/10610270802438820
e) Nosov R.V., Stoikov I.I. Macroheterocycles 2015, 8, 120–127;
https://doi.org/10.6060/mhc140929s
f) Dvořáková H., Lang J., Vlach J., Sýkora J., Čajan M., Himl M., Pojarová M., Stibor I., Lhoták P. J. Org. Chem. 2007, 72, 7157–7166.
https://doi.org/10.1021/jo070927i

25. a) Solovieva S.E., Muravev A.A., Zakirzyanov R.T., Latypov S.K., Antipin I.S., Konovalov A.I. Macroheterocycles 2012, 5, 17–22;
https://doi.org/10.6060/mhc2012.111048s
b) Muravev A.A., Solovieva S.E., Latypov S.K., Antipin I.S., Konovalov A.I. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 499–502;
https://doi.org/10.1080/10426507.2012.727516
c) Muravev A.A., Solovieva S.E., Kochetkov E.N., Mel'nikova N.B., Safiullin R.A., Kadirov M.K., Latypov S.K., Antipin I.S., Konovalov A.I. Macroheterocycles 2013, 6, 302–307.
https://doi.org/10.6060/mhc131269m

26. Lamouchi M., Jeanneau E., Chiriac R., Ceroni D., Meganem F., Brioude A., Coleman A.W., Desroches C. Tetrahedron Lett. 2012, 53, 2088–2090.
https://doi.org/10.1016/j.tetlet.2012.02.037

27. Solovieva S.E., Popova E.V., Omran A.O., Gubaidullin A.T., Kharlamov S.V., Latypov Sh.K., Antipin I.S., Konovalov A.I. Russ. Chem. Bull. 2011, 60, 486–498.
https://doi.org/10.1007/s11172-011-0076-0

28. Nakamura Y., Tanaka S., Serizawa R., Morohashi N., Hattori T. J. Org. Chem. 2011, 76, 2168–2179.
https://doi.org/10.1021/jo102566e

29. Latypov S., Epifanova N., Popova E., Vasilevsky S., Solovieva S., Antipin I., Konovalov A. Appl. Magn. Reson. 2011, 41, 467–475.
https://doi.org/10.1007/s00723-011-0264-y

Attachment	Size
mhc170304m.pdf	1.67 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Azide–Akyne Click Approach to the Preparation of Dendrimer–Type Multi(thia)calix[4]arenes with Triazole Linkers

References: