Acid-mediated synthesis of fully substituted 1,2,3-triazoles: Multicomponent coupling reactions, mechanistic study, synthesis of serine hydrolase inhibitor and its derivatives

Huan Zhang; Hiroki Tanimoto; Tsumoru Morimoto; Yasuhiro Nishiyama; Kiyomi Kakiuchi

doi:10.1016/j.tet.2014.10.076

Acid-mediated synthesis of fully substituted 1,2,3-triazoles: Multicomponent coupling reactions, mechanistic study, synthesis of serine hydrolase inhibitor and its derivatives

Huan Zhang, Hiroki Tanimoto^*, Tsumoru Morimoto, Yasuhiro Nishiyama, Kiyomi Kakiuchi

^*Corresponding author for this work

Biorecognition Chemistry

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

23 Scopus citations

Abstract

We describe the full details of multicomponent coupling reactions in acid-mediated synthesis of fully substituted 1,2,3-triazoles syntheses, and their applications to bioactive molecule synthesis. For substitution with wide range of nucleophiles, selection of acids or activating reagents was important, and various types of multicomponent coupling reactions were demonstrated, allowing functionalization with alcohols, amines, thiol, azide, and carbon nucleophiles. Four-component couplings including double triazolations were also tested. The efficiency of this method was demonstrated by the synthesis of serine hydrolase inhibitor and its novel substituted derivatives.

Original language	English
Pages (from-to)	9828-9835
Number of pages	8
Journal	Tetrahedron
Volume	70
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2014.10.076
State	Published - 2014/12/30

Keywords

Bioactive compounds
Multicomponent coupling reactions
Organic azides
Reaction mechanism
triazoles

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.10.076

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title = "Acid-mediated synthesis of fully substituted 1,2,3-triazoles: Multicomponent coupling reactions, mechanistic study, synthesis of serine hydrolase inhibitor and its derivatives",

abstract = "We describe the full details of multicomponent coupling reactions in acid-mediated synthesis of fully substituted 1,2,3-triazoles syntheses, and their applications to bioactive molecule synthesis. For substitution with wide range of nucleophiles, selection of acids or activating reagents was important, and various types of multicomponent coupling reactions were demonstrated, allowing functionalization with alcohols, amines, thiol, azide, and carbon nucleophiles. Four-component couplings including double triazolations were also tested. The efficiency of this method was demonstrated by the synthesis of serine hydrolase inhibitor and its novel substituted derivatives.",

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author = "Huan Zhang and Hiroki Tanimoto and Tsumoru Morimoto and Yasuhiro Nishiyama and Kiyomi Kakiuchi",

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AU - Zhang, Huan

AU - Tanimoto, Hiroki

AU - Morimoto, Tsumoru

AU - Nishiyama, Yasuhiro

AU - Kakiuchi, Kiyomi

PY - 2014/12/30

Y1 - 2014/12/30

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AB - We describe the full details of multicomponent coupling reactions in acid-mediated synthesis of fully substituted 1,2,3-triazoles syntheses, and their applications to bioactive molecule synthesis. For substitution with wide range of nucleophiles, selection of acids or activating reagents was important, and various types of multicomponent coupling reactions were demonstrated, allowing functionalization with alcohols, amines, thiol, azide, and carbon nucleophiles. Four-component couplings including double triazolations were also tested. The efficiency of this method was demonstrated by the synthesis of serine hydrolase inhibitor and its novel substituted derivatives.

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KW - Multicomponent coupling reactions

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KW - Reaction mechanism

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Acid-mediated synthesis of fully substituted 1,2,3-triazoles: Multicomponent coupling reactions, mechanistic study, synthesis of serine hydrolase inhibitor and its derivatives

Abstract

Keywords

ASJC Scopus subject areas

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