An Efficient Synthesis of 2-Diazo-2-(trimethylsilyl)ethanols and Their Application to Pyrazole Synthesis

Hari, Yoshiyuki; Tsuchida, Susumu; Sone, Ryosuke; Aoyama, Toyohiko

doi:10.1055/s-2007-990817

Synthesis

2007

DOI: 10.1055/s-2007-990817

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An Efficient Synthesis of 2-Diazo-2-(trimethylsilyl)ethanols and Their Application to Pyrazole Synthesis

Yoshiyuki Hari¹,

Susumu Tsuchida²,

Ryosuke Sone³

et al.

Abstract: Reaction of diazo(trimethylsilyl)methylmagnesium bromide with aldehydes or ketones gave 2-diazo-2-(trimethylsilyl)ethanols, which were applied to the synthesis of di-and trisubstituted pyrazoles via [3+2] cycloaddition reaction with ethyl propiolate or dimethyl acetylenedicarboxylate.

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Cited by 7 publications

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Cu_1.5PMo₁₂O₄₀‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles

Yang

et al. 2018

Applied Organom Chemis

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A convenient and direct approach has been developed for the preparation of pyrazole derivatives by the condensation cyclization of hydrazines/hydrazide and 1,3-diketones in the presence of Cu 1.5 PMo 12 O 40 (0.33 mol%) under mild conditions (r.t.-60°C, 10-30 min). Notably, the reaction was found to be scalable as 99% yield was obtained when the reaction was performed at a 5-mmol scale. This solvent-free and halogen-free catalytic system represents an effective economic and environmentally friendly method for the construction of pyrazoles.

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Cu_1.5PMo₁₂O₄₀‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles

Yang

et al. 2018

Applied Organom Chemis

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Synthesis of Functionalized Pyrazoles via 1,3‐Dipolar Cycloaddition of α‐Diazo‐β‐ketophosphonates, Sufones and Esters with Electron‐Deficient Alkenes

Baiju

Namboothiri

2017

The Chemical Record

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1,3-Dipolar cycloaddition of diazo compounds with olefinic substrates is a promising atom-economic strategy for the construction of functionalized pyrazoles. Over the last few years, our group has been engaged in the synthesis of phosphonyl/sulfonylpyrazoles and pyrazole esters by employing Bestmann-Ohira Reagent (BOR) and its sulfur and ester analogs as 1,3-dipole precursors with various dipolarophiles. This account describes the novel synthetic methods developed in our laboratory, in the perspective of closely related work by others, for the synthesis of phosphonyl/sulfonylpyrazoles, pyrazole esters and the total synthesis of Withasomnine, a natural product, by using 1,3-dipolar cycloaddition as the key step.

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Engineering in amino acid-functionalized double-layer heteropolymolybdates: from structural control to catalytic activity

et al. 2023

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An Efficient Synthesis of 2-Diazo-2-(trimethylsilyl)ethanols and Their Application to Pyrazole Synthesis

Abstract: Reaction of diazo(trimethylsilyl)methylmagnesium bromide with aldehydes or ketones gave 2-diazo-2-(trimethylsilyl)ethanols, which were applied to the synthesis of di-and trisubstituted pyrazoles via [3+2] cycloaddition reaction with ethyl propiolate or dimethyl acetylenedicarboxylate.

Cited by 7 publications

References 5 publications

Cu_1.5PMo₁₂O₄₀‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles

Cu_1.5PMo₁₂O₄₀‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles

Synthesis of Functionalized Pyrazoles via 1,3‐Dipolar Cycloaddition of α‐Diazo‐β‐ketophosphonates, Sufones and Esters with Electron‐Deficient Alkenes

Engineering in amino acid-functionalized double-layer heteropolymolybdates: from structural control to catalytic activity

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An Efficient Synthesis of 2-Diazo-2-(trimethylsilyl)ethanols and Their Application to Pyrazole Synthesis

Abstract: Reaction of diazo(trimethylsilyl)methylmagnesium bromide with aldehydes or ketones gave 2-diazo-2-(trimethylsilyl)ethanols, which were applied to the synthesis of di-and trisubstituted pyrazoles via [3+2] cycloaddition reaction with ethyl propiolate or dimethyl acetylenedicarboxylate.

Cited by 7 publications

References 5 publications

Cu1.5PMo12O40‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles

Cu1.5PMo12O40‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles

Synthesis of Functionalized Pyrazoles via 1,3‐Dipolar Cycloaddition of α‐Diazo‐β‐ketophosphonates, Sufones and Esters with Electron‐Deficient Alkenes

Engineering in amino acid-functionalized double-layer heteropolymolybdates: from structural control to catalytic activity

Contact Info

Product

Resources

About

Cu_1.5PMo₁₂O₄₀‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles

Cu_1.5PMo₁₂O₄₀‐catalyzed condensation cyclization for the synthesis of substituted pyrazoles