- Direct access to 1,4-disubstituted 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated esters with azides
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DBU-catalyzed organocatalytic 1,3-dipolar cycloaddition reactions of α,β-unsaturated esters with azides have been developed. This strategy generates 1,4-disubstituted 1,2,3-triazoles in high yields with high regioselectivities. It is demonstrated that some of these products can be transformed into important pharmaceutical agents.
- Li, Wenjun,Zhou, Xiao,Luan, Yepeng,Wang, Jian
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p. 88816 - 88820
(2015/11/09)
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- Copper(II)-catalyzed conversion of aryl/heteroaryl boronic acids, boronates, and trifluoroborates into the corresponding azides: Substrate scope and limitations
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We report the copper(II)-catalyzed conversion of organoboron compounds into the corresponding azide derivatives. A systematic series of phenylboronic acid derivatives is evaluated to examine the importance of steric and electronic effects of the sub-stituents on reaction yield as well as functional group compatibility. Heterocyclic substrates are also shown to participate in this mild reaction while compounds incorporating B-C(sp3) bonds are unreactive under the reaction conditions. The copper(II)-catalyzed boronic acid-azide coupling reaction is further extended to both boronate esters and potassium organotrifluoroborate salts. The method described herein complements existing procedures for the preparation of aryl azides from the respective amino, triazene, and halide derivatives and we expect that it will greatly facilitate copper- and ruthenium-catalyzed azide-alkyne cycloaddition reactions for the preparation of diversely functionalized 1-aryl- or 1-heteroaryl-1,2,3- triazoles derivatives. Georg Thieme Verlag Stuttgart.
- Grimes, Kimberly D.,Gupte, Amol,Aldrich, Courtney C.
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experimental part
p. 1441 - 1448
(2010/10/03)
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- Antiplatelet properties of novel N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone derivatives
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This paper describes the design, synthesis and pharmacological evaluation of new N-acylhydrazone (NAH) compounds, belonging to the N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone class (2a-p). Classical heteroaromatic ring bioisosterism strategies wer
- Cunha, Anna C.,Figueiredo, Juliana M.,Tributino, Jorge L. M.,Miranda, Ana L. P.,Castro, Helena C.,Zingali, Russolina B.,Fraga, Carlos A. M.,De Souza, Maria Cecilia B. V.,Ferreira, Vitor F.,Barreiro, Eliezer J.
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p. 2051 - 2059
(2007/10/03)
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- Arylazide cycloaddition to methyl propiolate: DFT-based quantitative prediction of regioselectivity
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Several 1-(4-substituted)-phenyl-4- or 5-methoxycarbonyl-1,2,3-triazoles have been synthesized by 1,3-dipolar cycloaddition of the corresponding arylazides to methyl propiolate in carbon tetrachloride. The regioselectivity of these reactions cannot be rat
- Molteni, Giorgio,Ponti, Alessandro
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p. 2770 - 2774
(2007/10/03)
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