Transition metal-free steric controlled one-pot synthesis of highly substituted N -amino 1,2,3-triazole derivatives via diazo transfer reaction from β-keto esters

Nagarajan, Rajendran; Jayashankaran, Jayadevan; Emmanuvel, Lourdusamy

doi:10.1016/j.tetlet.2016.04.112

Cited by 12 publications

(5 citation statements)

References 43 publications

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“…Application of a similar strategy by the change of azide to imidazole sulfonyl azide with β-keto esters provides an efficient one-pot practical method for N -amino-triazole synthesis ( Nagarajan et al, 2016 ). As shown in Supplementary Figure S3A , hydrazine ( 21 ) was obtained from β-keto esters ( 20 ), which on treatment with imidazole sulfonyl azide catalyzed by DBU-furnished 1,2,3-triazoles ( 22) containing nitrogen atom at the 1-position.…”

Section: Synthetic Approachesmentioning

confidence: 99%

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Matin

Chakraborty

Rahman

et al. 2022

Front. Mol. Biosci.

144

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Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Structurally, there are two types of five-membered triazoles: 1,2,3-triazole and 1,2,4-triazole. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities. These are also important in organocatalysis, agrochemicals, and materials science. Thus, they have a broad range of therapeutic applications with ever-widening future scope across scientific disciplines. However, adverse events such as hepatotoxicity and hormonal problems lead to a careful revision of the azole family to obtain higher efficacy with minimum side effects. This review focuses on the structural features, synthesis, and notable therapeutic applications of triazoles and related compounds.

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Section: Synthetic Approachesmentioning

confidence: 99%

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Matin

Chakraborty

Rahman

et al. 2022

Front. Mol. Biosci.

144

View full text Add to dashboard Cite

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“…03, 144.56, 139.12, 138.84, 134.34, 131.20, 130.57, 130.41, 130.06, 129.01, 128.09, 123.45, 117.21, 62.82, 14. 500 MHz, CDCl3): δ 8.77 (s, 1H), 115. 23,105.39,103.72,100.54,14.24,11.63. HRMS (ESI): m/z [M + H] + calcd.…”

Section: Methodsmentioning

confidence: 99%

“…Cunha et al [22] reported synthesis of 1-arylamino-1,2,3-triazole from diazo carbonyl compounds. Recently, we reported the synthesis of N-Boc protected 1-amino-1,2,3-triazole [23] via diazo transfer reaction on β-keto ester derived hydrazones. In this communication, we report the synthesis of 1-arylamino 1,2,3-triazole derivatives and cleavage of N-N bond of them to obtain 4,5-disubstituted 1,2,3-triazole under mild reduction condition using H2, Pd/C as catalyst.…”

Section: Introductionmentioning

confidence: 99%

Unusual Cleavage of N-N Bond of 1-Arylamino-1,2,3-triazole Derivatives: A Simple and Alternate Approach to 4,5-Disubstituted-1H-1,2,3-triazoles

Nagarajan

Emmanuvel

2019

Asian J. Chem.

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“…The steps sequence in a «diazo» approach to 1,2,3-triazoles can be reversed so that imine is formed first and then undergoes a diazo transfer reaction. In 2016, the Emmanuvel group developed a one-pot procedure for the synthesis of N -aminotriazoles 365 from β -ketocarbonyl compounds 364 and tert -butyl carbazate [ 179 ]. The reaction also worked well with 2,4-dinitrophenylhydrazine 366 .…”

Section: Azoles With Three Heteroatomsmentioning

confidence: 99%

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

et al. 2021

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Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.

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Transition metal-free steric controlled one-pot synthesis of highly substituted N -amino 1,2,3-triazole derivatives via diazo transfer reaction from β-keto esters

Cited by 12 publications

References 43 publications

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Unusual Cleavage of N-N Bond of 1-Arylamino-1,2,3-triazole Derivatives: A Simple and Alternate Approach to 4,5-Disubstituted-1H-1,2,3-triazoles

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

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