Electrochemical NaI-mediated one-pot synthesis of guanidines from isothiocyanates <i>via</i> tandem addition-guanylation

Huynh, Thao Nguyen Thanh; Nguyen, Khuyen Thu; Sukwattanasinitt, Mongkol; Wacharasindhu, Sumrit

doi:10.1039/d3ob01113e

Cited by 4 publications

(1 citation statement)

References 57 publications

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“…Therefore, numerous synthetic methods have been developed using iodide-mediated C–N bond formation under electrochemical processes to prepare various N -heterocycle compounds, including isatins, , oxadiazoles, aziridines, , arizines, quinazolinones, , indoles, , indolines, − etc . Lately, our group has successfully developed the synthesis of various compounds, including amides, 2-aminobenzoxazoles, chalcone, and guanidines, using the iodide-mediated electrochemical approach. Continuing our research in this area, we aim to expand this method to synthesize N -substituted 2-aminobenzimidazoles 3 through an addition–desulfurization process between N -substituted o -phenylenediamines 1 and isothiocyanates 2 (Scheme b).…”

Section: Introductionmentioning

confidence: 99%

NaI-Mediated Electrochemical Cyclization–Desulfurization for the Synthesis of N-Substituted 2-Aminobenzimidazoles

Nguyen,

Huynh,

Ratanathawornkiti

et al. 2023

J. Org. Chem.

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An electrochemical method for the synthesis of Nsubstituted 2-aminobenzimidazoles through a NaI-mediated desulfurization−cyclization process is reported. This electrosynthesis method utilizes cost-effective NaI as both a mediator and an electrolyte in a catalytic amount (0.2 equiv), replacing traditional oxidizing reagents. N-Substituted o-phenylenediamines and isothiocyanates undergo a thiourea formation/cyclization/desulfurization process to provide N-substituted 2-aminobenzimidazoles (55 examples, up to 98% yield) in a single reaction vessel. Importantly, this electrochemical methodology is applicable to gram-scale synthesis, maintaining reaction efficiency.

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Section: Introductionmentioning

confidence: 99%

NaI-Mediated Electrochemical Cyclization–Desulfurization for the Synthesis of N-Substituted 2-Aminobenzimidazoles

Nguyen,

Huynh,

Ratanathawornkiti

et al. 2023

J. Org. Chem.

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Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Yu,

Hao,

Liu

et al. 2024

Adv Synth Catal

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A one‐pot method has been developed for synthesizing diverse substituted 5‐aminotetrazoles via the electrochemically induced desulfurizative addition‐cyclization of thioureas with azidotrimethylsilane. This methodology enables the construction of C–N and N–N bonds under mild reaction conditions without transition metal catalysts or external oxidizing agents. The applicability of this approach is demonstrated by its broad substrate scope, compatibility with various functional groups, scalability to gram‐scale synthesis, and practicality evidenced by the synthesis of an antibacterial agent

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Metal-Free Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides

Mondal,

Sati,

Hashim

et al. 2024

J. Org. Chem.

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A metal-free process has been developed for the sustainable synthesis of medicinally important sulfonylureas in one pot via the direct reaction of sulfonamides with amides in green solvent (DMC). The reaction proceeded efficiently at room temperature, and the products were obtained in good to excellent yields. The use of readily accessible, inexpensive, and environmentally benign starting materials and reagents, metal-free mild reaction conditions, wide substrate scope, tolerance to air and moisture, operational simplicity, and good atom economy are the salient features of this reaction protocol. Gram-scale synthesis of antidiabetic drugs tolbutamide and chlorpropamide in excellent yields further revealed the practical utility of this procedure. Additionally, the synthetic value of this straightforward method is showcased by the late-stage modification of drug molecules, including drug−drug conjugation with good yields. Preliminary mechanistic studies indicated the in situ generation of an isocyanate intermediate, which further reacts with sulfonamide to form sulfonylurea. As compared to other related methods reported for sulfonylurea synthesis, the current method obviates the requirement of traditional multistep protocols involving isolation of hazardous isocyanates and avoids the use of toxic phosgene.

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Electrochemical NaI-mediated one-pot synthesis of guanidines from isothiocyanates via tandem addition-guanylation

Abstract: In this study, we present an electrochemical approach for the synthesis of guanidines from isothiocyanates and amines in a single reaction vessel.

Cited by 4 publications

References 57 publications

NaI-Mediated Electrochemical Cyclization–Desulfurization for the Synthesis of N-Substituted 2-Aminobenzimidazoles

NaI-Mediated Electrochemical Cyclization–Desulfurization for the Synthesis of N-Substituted 2-Aminobenzimidazoles

Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Metal-Free Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides

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