Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on 1,3-dipolar cycloaddition

Abstract

Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on the 1,3-dipolar cycloaddition of substituted benzyl azides to tetra(propargyloxy)calix[4]arenes in the presence of copper iodide was carried out. The presence of the p-methoxybenzyl substituent in the triazole ring leads to a dramatic (more than tenfold) increase in the fluorescence of the corresponding macrocycle in a region of 290-310 nm.

Original language	English
Pages (from-to)	767-772
Number of pages	6
Journal	Russian Chemical Bulletin
Volume	62
Issue number	3
DOIs	https://doi.org/10.1007/s11172-013-0104-3
Publication status	Published - 1 Mar 2013
Externally published	Yes

Keywords

1,2,3-triazoles
1,3-dipolar cycloaddition
benzyl azides
calix[4]arenes
fluorescence

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1007/s11172-013-0104-3

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@article{2dc177d325b7494bb10ecfe18e7ea51e,

title = "Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on 1,3-dipolar cycloaddition",

abstract = "Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on the 1,3-dipolar cycloaddition of substituted benzyl azides to tetra(propargyloxy)calix[4]arenes in the presence of copper iodide was carried out. The presence of the p-methoxybenzyl substituent in the triazole ring leads to a dramatic (more than tenfold) increase in the fluorescence of the corresponding macrocycle in a region of 290-310 nm.",

keywords = "1,2,3-triazoles, 1,3-dipolar cycloaddition, benzyl azides, calix[4]arenes, fluorescence",

author = "Burilov, {V. A.} and Epifanova, {N. A.} and Popova, {E. V.} and Vasilevsky, {S. F.} and Solovieva, {S. E.} and Antipin, {I. S.} and Konovalov, {A. I.}",

year = "2013",

month = mar,

day = "1",

doi = "10.1007/s11172-013-0104-3",

language = "English",

volume = "62",

pages = "767--772",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer New York",

number = "3",

}

TY - JOUR

T1 - Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on 1,3-dipolar cycloaddition

AU - Burilov, V. A.

AU - Epifanova, N. A.

AU - Popova, E. V.

AU - Vasilevsky, S. F.

AU - Solovieva, S. E.

AU - Antipin, I. S.

AU - Konovalov, A. I.

PY - 2013/3/1

Y1 - 2013/3/1

N2 - Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on the 1,3-dipolar cycloaddition of substituted benzyl azides to tetra(propargyloxy)calix[4]arenes in the presence of copper iodide was carried out. The presence of the p-methoxybenzyl substituent in the triazole ring leads to a dramatic (more than tenfold) increase in the fluorescence of the corresponding macrocycle in a region of 290-310 nm.

AB - Regioselective synthesis of 1,2,3-triazolyl derivatives of calix[4]arenes based on the 1,3-dipolar cycloaddition of substituted benzyl azides to tetra(propargyloxy)calix[4]arenes in the presence of copper iodide was carried out. The presence of the p-methoxybenzyl substituent in the triazole ring leads to a dramatic (more than tenfold) increase in the fluorescence of the corresponding macrocycle in a region of 290-310 nm.

KW - 1,2,3-triazoles

KW - 1,3-dipolar cycloaddition

KW - benzyl azides

KW - calix[4]arenes

KW - fluorescence

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U2 - 10.1007/s11172-013-0104-3

DO - 10.1007/s11172-013-0104-3

M3 - Article

AN - SCOPUS:84891815156

VL - 62

SP - 767

EP - 772

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 3