Synthesis of Macrocycles Containing 1,2,3-Triazole Motifs

Ludmila Hradilová; Martin Grepl; Jan Hlaváč; Antonín Lyčka; Pavel Hradil

doi:10.1055/s-0031-1290760

Synthesis, Table of Contents

Synthesis 2012; 44(9): 1398-1404
DOI: 10.1055/s-0031-1290760

paper

Synthesis of Macrocycles Containing 1,2,3-Triazole Motifs

Ludmila Hradilová

^aDepartment of Organic Chemistry, Palacky University, Tr. 17. Listopadu 12, 771 46 Olomouc, Czech Republic

,

Martin Grepl

^aDepartment of Organic Chemistry, Palacky University, Tr. 17. Listopadu 12, 771 46 Olomouc, Czech Republic

^bFarmak a.s., Na Vlcinci 3, 771 17 Olomouc, Czech Republic, Fax: +420(58)231424 Email: hradil@farmak.cz

,

Jan Hlaváč

^aDepartment of Organic Chemistry, Palacky University, Tr. 17. Listopadu 12, 771 46 Olomouc, Czech Republic

,

Antonín Lyčka

^cResearch Institute for Organic Syntheses, Rybitvi 296, 533 54 Pardubice, Czech Republic

^dUniversity of Hradec Kralove, Faculty of Science, Rokitanského 62, 500 03 Hradec Králove 3, Czech Republic

,

Pavel Hradil*

^aDepartment of Organic Chemistry, Palacky University, Tr. 17. Listopadu 12, 771 46 Olomouc, Czech Republic

^bFarmak a.s., Na Vlcinci 3, 771 17 Olomouc, Czech Republic, Fax: +420(58)231424 Email: hradil@farmak.cz

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Abstract

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Abstract

A new procedure for the preparation of macrocycles containing 1,2,3-triazole motifs is developed. The macrocyclic precursor is constructed by repetition of a series of steps which include cycloaddition of an azide with an alkyne, alkylation of a carboxylic acid with propargyl bromide and formation of an azide from an amino group. The order of the steps and the size of the connected fragments are determined by the desired ring size. Chromatographic purification techniques for the poorly soluble final products are also described.

Key words

macrocycles - 1,2,3-triazole - cycloaddition - azidobenzoate - propargyl ester

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References

References
1 Wessjohann LA, Ruijter E, Garcia-Rivera D, Brandt W. Mol. Diversity 2005; 9: 171
2 Tyndall JD. A, Fairlie DP. Curr. Med. Chem. 2001; 8: 893
3 Nishino N, Wagner RN, Lindsey JN. J. Org. Chem. 1996; 61: 7534
4 Hellier PC, Bradshaw JS, Young JJ, Zhang XX, Izatt RM. J. Org. Chem. 1996; 61: 7270
5 Rajakumar P, Murali V. Tetrahedron 2000; 56: 7995
6 Kim SH, Choi SH, Kim J, Lee SJ, Quang DT, Kim JS. Org. Lett. 2010; 12: 560
7 Pirali T, Tron GC, Zhu J. Org. Lett. 2006; 8: 4145
8 Chandrasekhar S, Rao CL, Nagesh C, Reddy CR, Sridhar B. Tetrahedron Lett. 2007; 48: 5869
9 Yanai H, Taguchi T. Tetrahedron Lett. 2005; 46: 8639
10 Ray A, Manoj K, Bhadbhade MM, Mukhopadhyay R, Bhattacharjya A. Tetrahedron Lett. 2006; 47: 2775
11 Shao C, Wang X, Xu J, Zhao J, Zhang Q, Hu Y. J. Org. Chem. 2010; 75: 7002
12 Chen H, Zuo S, Tang X, Zhao M, Lu Y, Chen L, Liu J, Liu Y, Liu D, Zhang S, Li T, Wang X. Eur. J. Med. Chem. 2011; 46: 4709
13 Majumdar KC, Ray K. Synthesis 2011; 3767
14 Hradilová L, Grepl M, Hlaváč J, Lyčka A, Hradil P. J. Heterocycl. Chem. 2012; in press
15 Garanti L, Molteni G, Zecchi G. Heterocycles 1994; 38: 291
16 More SS, Shanmughapriya D, Lingam Y, Patel NB. Synth. Commun. 2009; 39: 2058