Microwave-assisted one-pot quick synthesis of 1-monosubstituted 1,2,3-triazoles from arylboronic acids, sodium azide and
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Ó Indian Academy of Sciences Sadhana (0123456789().,-volV)FT3](0123456 789().,-volV)
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Microwave-assisted one-pot quick synthesis of 1-monosubstituted 1,2,3-triazoles from arylboronic acids, sodium azide and 3-butyn-2ols ZHONGLIN DU*
, FENRUI LI, LI LI and RAN LI
Kunming Metallurgy College, No. 388 Xuefu Road, Kunming 650033, People’s Republic of China E-mail: [email protected] MS received 16 August 2020; revised 30 September 2020; accepted 3 October 2020
Abstract. Microwave-assisted one-pot quick synthesis to 1-monosubstituted 1,2,3-triazoles was achieved with good to excellent yields using the widely available arylboronic acids, sodium azide and 3-butyn-2-ols within 15 min. This method features high efficient and facile as organic azides, acetylene gas and harsh conditions were avoided. Keywords. microwave-assisted; one-pot; 1-monosubstituted 1,2,3-triazole; 3-butyn-2-ols.
1. Introduction 1,2,3-Triazoles are an important kind of heterocyclics widely applied in many fields such as biological science,1 material field,2 medicinal chemistry3 and synthetic methodologies.4 Particularly in recent years, they have played increasingly important roles in clinical and commercial drugs such as IDO (indoleamine 2,3-dioxygenase) inhibitors,5 antibiotics,6 HDIs (histone deacetylase inhibitors)7 and antiviral drugs (Figure 1).8 Though 1, 2, 3-triazoles were found more than 100 years ago, efficient strategies for the synthesis have been explored only in recent decades. The first method to construct the 1, 2, 3-triazole ring was Huisgen dipolar cycloaddition through the thermal process, giving 1,4- and 1,5-disubstituted regioisomers without regioselectivity.9 At the beginning of this century, Sharpless10 group achieved a copper-catalyzed 1,3dipolar cycloaddition reaction (CuAAC) between terminal alkynes and azides, reaching the regioselective construction of the 1, 4-disubstituted 1, 2, 3-triazoles. This method is very vigorous and led to many other similar approaches subsequently.11 Meanwhile, the synthesis for 1, 5-disubsituted 1, 2, 3-triazoles were reported, in which ruthenium, erbium, or base were usually applied as the catalyst.12 Lately, 1, 4,
5-trisubsituted 1, 2, 3-triazoles13 have been also synthesized mainly through a three-component system. While 1-monosubstituted 1, 2, 3-triazole derivatives, another particular branch of this heterocycles show various high values, mainly owing to its broad biological activities (Figure 1). Thus, the explorations for the constructions attract much attention recently. Acetylene gas is the most acknowledged substrate to serve as a partner of the CuAAC reaction with organic azides to generate 1-monosubstituted 1, 2, 3-triazoles, which was first reported by Liang group.14 Additionally, acetylene derivatives (such as trimethylsilylacetylene, ethynyltributyltin, sodium acetylide, calcium carbide, propiolic acid, and propargyl alcohol) and vinyl compounds (such as vinyl acetate, vinyl ethers, vinyl amines, and vinyl sulfoxides) have been proved to be reliable alternatives
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