Regioselective 1,3-dipolar cycloaddition of nitriles with nitrile imines generated from tetrazoles

Tomoya Miura; Kohei Hagiwara; Takayuki Nakamuro; Yuuya Nagata; Naoki Oku; Masahiro Murakami

doi:10.1246/CL.200634

Regioselective 1,3-dipolar cycloaddition of nitriles with nitrile imines generated from tetrazoles

Tomoya Miura, Kohei Hagiwara, Takayuki Nakamuro, Yuuya Nagata, Naoki Oku, Masahiro Murakami

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	131-135
Number of pages	5
Journal	Chemistry Letters
Volume	50
Issue number	1
DOIs	https://doi.org/10.1246/CL.200634
Publication status	Published - Jan 2021
Externally published	Yes

Keywords

Cycloaddition
Nitrile imines
Tetrazoles

ASJC Scopus subject areas

Chemistry(all)

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10.1246/CL.200634

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@article{4a466709121943a299c6583f3977c6ed,

title = "Regioselective 1,3-dipolar cycloaddition of nitriles with nitrile imines generated from tetrazoles",

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.",

keywords = "Cycloaddition, Nitrile imines, Tetrazoles",

author = "Tomoya Miura and Kohei Hagiwara and Takayuki Nakamuro and Yuuya Nagata and Naoki Oku and Masahiro Murakami",

note = "Funding Information: This work was supported in part by MEXT [Grants-in-Aid for Scientific Research (B) (20H02739) (TM)], JST-ERATO (No. JPMJER1903) (YN), and JSPS-WPI (YN). TN acknowledges JSPS fellowship for young scientists. Publisher Copyright: {\textcopyright} 2021 The Chemical Society of Japan",

year = "2021",

month = jan,

doi = "10.1246/CL.200634",

language = "English",

volume = "50",

pages = "131--135",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "1",

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TY - JOUR

T1 - Regioselective 1,3-dipolar cycloaddition of nitriles with nitrile imines generated from tetrazoles

AU - Miura, Tomoya

AU - Hagiwara, Kohei

AU - Nakamuro, Takayuki

AU - Nagata, Yuuya

AU - Oku, Naoki

AU - Murakami, Masahiro

N1 - Funding Information: This work was supported in part by MEXT [Grants-in-Aid for Scientific Research (B) (20H02739) (TM)], JST-ERATO (No. JPMJER1903) (YN), and JSPS-WPI (YN). TN acknowledges JSPS fellowship for young scientists. Publisher Copyright: © 2021 The Chemical Society of Japan

PY - 2021/1

Y1 - 2021/1

N2 - 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.

AB - 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.

KW - Cycloaddition

KW - Nitrile imines

KW - Tetrazoles

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U2 - 10.1246/CL.200634

DO - 10.1246/CL.200634

M3 - Article

AN - SCOPUS:85099194920

SN - 0366-7022

VL - 50

SP - 131

EP - 135

JO - Chemistry Letters

JF - Chemistry Letters

IS - 1

ER -

Regioselective 1,3-dipolar cycloaddition of nitriles with nitrile imines generated from tetrazoles

Abstract

Keywords

ASJC Scopus subject areas

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