Efficient in Situ Synthesis of 3,5-Disubstituted-1,2,4-triazoles Under Microwave-Assisted Conditions

Abstract

Based on an efficient in situ metal/ligand reaction, a serial of 3,5-disubstituted-1,2,4-triazoles were synthesized via cycloaddition of organonitriles and ammonia under microwave conditions. This synthetic protocol provides a concise and high-yield access to 3,5-disubstituted-1,2,4-triazoles in organic synthesis. Moreover, the tautomerism of the product was also investigated.

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GRAPHICAL ABSTRACT

Keywords:

• Cycloaddition
• 3,5-disubstituted-1,2,4-triazole
• in situ metal/ligand reaction
• microwave-assisted
• tautomerism

ACKNOWLEDGMENTS

We gratefully acknowledge the financial support from the National Natural Science Foundation of China (Grant No. 21173168), the Science Research Projects of Department of Shaanxi Provincial Government (Grant Nos. 2010JK882, 2010JQ2007, 11JS110, and 11JK0578), and the Natural Science Foundation of Shangluo University (Grant No. 12SKY012).

Notes

^a The reaction conditions were described as hydrothermal (the upper line) and the microwave-assisted (the lower line).

^b The yields are based on the organonitriles, and the yields were described as hydrothermal (the upper line) and microwave-assisted (the lower line).

^a

^b .

^a Symmetry operation: x + 1,y + 1,z.