2021Asian Journal of Organic ChemistryRequires access

Divergent Synthesis of 3,5‐Disubstituted Pyrazoles and α, β ‐Alkynic Hydrazone from Diarylpropynones and Carbazates

Qi Wang, Gang Hong, Zhicong Tang, Peng Yang, Yi Zhong, Yu Gong, Limin Wang

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Abstract

Abstract Yb(OTf) 3 catalyzed synthesis of pyrazoles by cyclization of 1,3‐diarylpropynones with carbazates was reported. In the presence of K 2 S 2 O 8 /TBAI as catalyst, α , β ‐alkynic hydrazone was obtained through the reactions from the same starting materials in up to 97% yields. Mechanistic studies indicated that propargyl hydrazone was not involved in pyrazole formation. The aggregation‐induced emission (AIE) characteristics of the pyrazoles were explored, demonstrating potential applications in the luminophoric materials.

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Abstract Yb(OTf) 3 catalyzed synthesis of pyrazoles by cyclization of 1,3‐diarylpropynones with carbazates was reported. In the presence of K 2 S 2 O 8 /TBAI as catalyst, α , β ‐alkynic hydrazone was obtained through the reactions from the same starting materials in up to 97% yields. Mechanistic studies indicated that propargyl hydrazone was not involved in pyrazole formation. The aggregation‐induced emission (AIE) characteristics of the pyrazoles were explored, demonstrating potential applications in the luminophoric materials.

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Available abstract

Abstract Yb(OTf) 3 catalyzed synthesis of pyrazoles by cyclization of 1,3‐diarylpropynones with carbazates was reported. In the presence of K 2 S 2 O 8 /TBAI as catalyst, α , β ‐alkynic hydrazone was obtained through the reactions from the same starting materials in up to 97% yields. Mechanistic studies indicated that propargyl hydrazone was not involved in pyrazole formation. The aggregation‐induced emission (AIE) characteristics of the pyrazoles were explored, demonstrating potential applications in the luminophoric materials.

Key concepts: Hydrazone, Chemistry, Pyrazole, Propargyl, Catalysis, Medicinal chemistry, Stereochemistry, Organic chemistry

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Divergent Synthesis of 3,5‐Disubstituted Pyrazoles and α, β ‐Alkynic Hydrazone from Diarylpropynones and Carbazates — Research Paper | ScholarLens