Regioselective 1,3-Dipolar Cycloaddition of Nitriles with Nitrile Imines Generated from Tetrazoles

• Tomoya Miura

  Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 , Japan

• Kohei Hagiwara

  Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 , Japan

• Takayuki Nakamuro

  Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 , Japan

• Yuuya Nagata

  Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 001-0021 , Japan

• Naoki Oku

  Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 , Japan

• Masahiro Murakami

  Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 , Japan

Abstract

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 1,3-dipolar cycloaddition with nitriles in a regioselective manner, forming the corresponding 1,2,4-triazoles.

Journal

• Chemistry Letters

  Chemistry Letters 50 (1), 131-135, 2020-10-06

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1361131421984200448
• NII Article ID: 130007966020
• DOI: 10.1246/cl.200634
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/50/1/131/56758505/cl.200634.pdf
• Data Source:
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