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ISSN 1998-9539

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. Konovalova
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 %.

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