Regioselective synthesis of 4-fluoro-1,5-substituted-1,2,3-triazoles from synthetic surrogates of 1-fluoroalkynes

10.26434/chemrxiv.9738656 ◽

2019 ◽

Author(s):

Sampad Jana ◽

Sweta Adhikari ◽

Michael Cox ◽

Sudeshna Roy

Keyword(s):

Catalytic Amount ◽

Regioselective Synthesis ◽

Cycloaddition Reactions ◽

Organic Azides

Here, we show that 1-fluoronitroalkenes can serve as synthetic surrogates of 1-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifloroacetic acid. This work provides the first regioselective method to access 4-fluoro-1,5-substituted-1,2,3-triazoles.

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Fluorinated 1,2,3-Triazoles from α-Fluoronitroalkenes as Surrogates of α-Fluoroalkynes via Regioselective Cycloaddition Reactions with Organic Azides

10.26434/chemrxiv.9738656.v1 ◽

2019 ◽

Author(s):

Sampad Jana ◽

Sweta Adhikari ◽

Michael Cox ◽

Sudeshna Roy

Keyword(s):

Trifluoroacetic Acid ◽

Catalytic Amount ◽

Cycloaddition Reactions ◽

Organic Azides

Here we show that 1-fluoronitroalkenes can serve as synthetic surrogates of 1-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid.

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Fluorinated 1,2,3-Triazoles from α-Fluoronitroalkenes as Surrogates of α-Fluoroalkynes via Regioselective Cycloaddition Reactions with Organic Azides

10.26434/chemrxiv.9738656.v2 ◽

2019 ◽

Author(s):

Sampad Jana ◽

Sweta Adhikari ◽

Michael Cox ◽

Sudeshna Roy

Keyword(s):

Trifluoroacetic Acid ◽

Catalytic Amount ◽

Cycloaddition Reactions ◽

Organic Azides

Here we show that 1-fluoronitroalkenes can serve as synthetic surrogates of 1-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid.

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Regioselective Synthesis of Novel 4,4′-and 5,5′-bi-(1,2,4-triazole) Derivatives

Journal of Chemical Research ◽

10.3184/030823407x237876 ◽

2007 ◽

Vol 2007 (8) ◽

pp. 472-474 ◽

Cited By ~ 10

Author(s):

Ahmad M. Farag ◽

Kamal M. Dawood ◽

Nabila A. Khedr

Keyword(s):

Regioselective Synthesis ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions ◽

Triazole Derivatives

A regioselective synthesis is reported of a series of polysubstituted 1,2,4-triazoles and 4,4′- and 5,5′-bi-(1,2,4-triazoles) via 1,3-dipolar cycloaddition reactions of nitrilimines with some aza- and diaza-butadiene derivatives.

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The synthesis of five membered N-heterocycles by cycloadditions of nitroalkenes with (in)organic azides and other 1,3-dipoles

Synthesis ◽

10.1055/a-1547-0196 ◽

2021 ◽

Author(s):

Shandev Pookkandam Parambil ◽

Santhini Pulikkal Veettil ◽

Wim Dehaen

Keyword(s):

Research Area ◽

Cycloaddition Reactions ◽

Powerful Method ◽

Organic Azides

Cycloaddition reactions have emerged as rapid and powerful method for constructing heterocycles and carbocycles. [3+2] Cycloadditions of nitroalkenes with various 1,3-dipoles have been an interesting research area for many organic chemists. This review outlines the synthesis of N-substituted and NH-1,2,3-triazoles along with other five membered N-heterocycles through cycloaddition reactions of nitroalkene. 1. Introduction 2. Synthesis of 1,2,3-triazoles 2.1.Synthesis of NH-1,2,3-triazoles 2.2.Synthesis of N-substituted 1,2,3-triazoles 3. Synthesis of Pyrrolidines and Pyrroles 4. Synthesis of Pyrazoles 5. Conclusion

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