PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
SHORT COMMUNICATION
Synthesis of 1,2,3-triazolyl-5-diethylphosphonate by domino reaction
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Anna Tripolszky, Emese Toth, and Erika Balint
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
ABSTRACT
ARTICLE HISTORY
Received 1 October 2018
Accepted 9 November 2018
The synthesis of 1,2,3-triazolyl-5-diethylphosphonate was studied by the domino reaction of benzyl
azide, phenylacetylene and diethyl phosphite. The effect of the reaction stoichiometry, the atmos-
phere and the amount of the catalyst were investigated.
KEYWORDS
1,2,3-triazolyl-5-diethyl-
phosphonate; domino
reaction; Cu(I) catalyst;
triazole ring
GRAPHICAL ABSTRACT
Over the last years, the chemistry of heterocyclic amino- ments were carried out for the domino reaction of benzyl
phosphonates has received an intense interest due to their azide, phenylacetylene and diethyl phosphite in the presence
versatile bioactivities.[1] Some triazolylphosphonate derivatives of CuCl as a catalyst and trimethylamine as a base, at room
have been used for protein binding studies[2] and their ana- temperature in acetonitrile. The effect of the reaction stoi-
logs were suitable for bioconjugation.[3] One of the most chiometry, the atmosphere and the amount of the catalyst
effective tools for the preparation of heterocyclic amino- were studied. First, the domino reaction was performed
phosphonates is multicomponent reactions (MCR). These under a nitrogen atmosphere, and instead of the desired tri-
transformations have several benefits, such as high atom azolylphosphonate (D), 1-benzyl-4-phenyl-1H-1,2,3-triazole
(E) was the main product (68%), which was formed by the
click reaction of benzyl azide and phenylacetylene (Table 1/
Entry 1). Carrying out the reaction in an open-air flask, the
ratio was reversed, and the triazolylphosphonate (D) was
formed in 53%, along with 7% of diethyl (phenylethynyl)-
economy, fast and simple accomplishment, ability to save
time and energy and being environmentally-friendly.[4,5] The
domino reaction belongs to the group of MCR but despite its
outstanding properties, only one example can be found for
the synthesis of triazolylphosphonates by domino reaction.[6]
In this work, the synthesis of 1,2,3-triazolyl-5-diethyl- phosphonate (Table 1/Entry 2). Increasing the amount of
phosphonate was investigated (Table 1). Preliminary experi- the diethyl phosphite to two equivalents, the proportion of
Table 1. Domino reaction of benzyl azide, phenylacetylene and diethyl phosphite.
Ã
A
B
C
Catalyst
Product composition [%]
Entry
Equiv.
Atmosphere
D
E
F
1
2
3
4
5
6
Ã
1
1
1
1
1
1
1.1
1.1
1.1
1.1
1.1
1.1
1.1
1.1
2
2
3
0.1
0.1
0.1
0.1
0.1
0.15
N2
air
air
32
53
71
83
54
65
68
39
26
14
43
31
1
7
3
3
3
4
air bubbling
air bubbling
air bubbling
2
Based on HPLC (222 nm).
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CONTACT Anna Tripolszky
ß 2018 Taylor & Francis Group, LLC
Tripolszky, Anna
