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

Synthesis ◽  
2021 ◽  
Author(s):  
Shandev Pookkandam Parambil ◽  
Santhini Pulikkal Veettil ◽  
Wim Dehaen

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

2019 ◽  
Author(s):  
Sampad Jana ◽  
Sweta Adhikari ◽  
Michael Cox ◽  
Sudeshna Roy

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.


2019 ◽  
Author(s):  
Sampad Jana ◽  
Sweta Adhikari ◽  
Michael Cox ◽  
Sudeshna Roy

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.


2022 ◽  
Author(s):  
A. J. Paterson ◽  
T. Beke-Somfai ◽  
N. Kann

AbstractUnder ruthenium catalysis, 1,5-disubstituted 1,2,3-triazoles can be accessed with high selectivity from terminal alkynes and organic azides via a ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC) reaction. These conditions also allow the use of internal alkynes, providing access to 1,4,5-trisubstituted 1,2,3-triazoles. This chapter reviews the scope and limitations of the RuAAC reaction, as well as selected applications. A brief mention of azide–alkyne cycloaddition reactions catalyzed by other metals is also included.


ChemInform ◽  
2007 ◽  
Vol 38 (24) ◽  
Author(s):  
Muriel Compain-Batissou ◽  
Jacques Gentili ◽  
Nadia Walchshofer ◽  
Monique Domard ◽  
Bernard Fenet ◽  
...  

2019 ◽  
Author(s):  
Sampad Jana ◽  
Sweta Adhikari ◽  
Michael Cox ◽  
Sudeshna Roy

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.


2019 ◽  
Author(s):  
Sampad Jana ◽  
Sweta Adhikari ◽  
Michael Cox ◽  
Sudeshna Roy

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.


1989 ◽  
Vol 26 (5) ◽  
pp. 1461-1468 ◽  
Author(s):  
Sultan T. Abu-Orabi ◽  
M. Adnan Atfah ◽  
Ibrahim Jibril ◽  
Fakhri M. Mari'i ◽  
Amer Al-Sheikh Ali

Heterocycles ◽  
2007 ◽  
Vol 71 (1) ◽  
pp. 27 ◽  
Author(s):  
Zouhair Bouaziz ◽  
Muriel Compain-Batissou ◽  
Jacques Gentili ◽  
Nadia Walchshofer ◽  
Monique Domard ◽  
...  

ChemInform ◽  
1990 ◽  
Vol 21 (11) ◽  
Author(s):  
S. T. ABU-ORABI ◽  
M. A. ATFAH ◽  
I. JIBRIL ◽  
F. M. MARI'I ◽  
A. A.-S. ALI

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