Journal
CHEMISTRY LETTERS
Volume 50, Issue 1, Pages 131-135Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/cl.200634
Keywords
Cycloaddition; Nitrile imines; Tetrazoles
Categories
Funding
- MEXT [20H02739]
- JST-ERATO [JPMJER1903]
- JSPS-WPI
- JSPS
- Grants-in-Aid for Scientific Research [20H02739] Funding Source: KAKEN
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A method for the synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles is described. The reaction involves ring-chain tautomerization, denitrogenation, and 1,3-dipolar cycloaddition to achieve regioselective formation of the desired triazoles.
A synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles is reported. When 5-aryltetrazoles are triflylated in the presence of nitriles, the resulting 5-aryl-2-triflyltetrazoles thermally generate N-triflyl-nitrile imines through a sequence of ring-chain tautomerization and denitrogenation. The N-triflyl-nitrile imines immediately undergo 1,3dipolar cycloaddition with nitriles in a regioselective manner, forming the corresponding 1,2,4-triazoles.
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