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. 2022 Sep 15:18:1249-1255.
doi: 10.3762/bjoc.18.130. eCollection 2022.

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

Shang-Feng Yang #  1 , Pei Li #  1 , Zi-Lin Fang  1 , Sen Liang  1 , Hong-Yu Tian  1 , Bao-Guo Sun  1 , Kun Xu  2 , Cheng-Chu Zeng  2
Affiliations

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

Shang-Feng Yang et al. Beilstein J Org Chem. .

Abstract

The electrochemical preparation of 2-aminothiazoles has been achieved by the reaction of active methylene ketones with thioureas assisted by ᴅʟ-alanine using NH4I as a redox mediator. The electrochemical protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically, the in situ generated α-iodoketone was proposed to be the key active species.

Keywords: 2-aminothiazoles; electrosynthesis; halide ion; indirect electrolysis.

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Figures

Scheme 1
Scheme 1
Methods for the synthesis of thiazoles using active methylene ketones as starting materials.
Scheme 2
Scheme 2
Substrate scope. Reaction conditions: 1 (2 mmol), 2 (1 mmol), NH4I (0.1 mmol), ᴅʟ-alanine (1 mmol), LiClO4 (0.5 mmol) in DMSO 1 mL + H2O 14 mL, undivided cell, graphite plate anode and cathode, 30 °C, 5 mA/cm2, 6 F/mol; isolated yields are given. a8 F/mol.
Scheme 3
Scheme 3
Up-scaling experiment.
Scheme 4
Scheme 4
Control experiments.
Scheme 5
Scheme 5
The proposed mechanism for the one-pot electrochemical synthesis of 2-aminothiazoles mediated by NH4I.
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