Base-mediated synthesis of cyclic dithiocarbamates from 1-amino-3-chloropropan-2-ol derivatives and carbon disulfide

Toda, Yasunori; Iwasaki, Masaya; Suga, Hiroyuki

doi:10.1039/d3ob01070h

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob01070h

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Base-mediated synthesis of cyclic dithiocarbamates from 1-amino-3-chloropropan-2-ol derivatives and carbon disulfide

Yasunori Toda¹,

Masaya Iwasaki²,

Hiroyuki Suga³

Abstract: An efficient method for the preparation of six-membered cyclic dithiocarbamates is described, in which triethylamine effectively promotes the reaction of 1-amino-3-chloropropan-2-ol derivatives with carbon disulfide. On the basis of the...

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2024

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Cited by 2 publications

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Emerging Trends for the Direct Synthesis of Dithiocarbamates

He,

Zhou,

Liu

2024

Adv Synth Catal

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Dithiocarbamates are common structural motifs in various bioactive compounds, attracting considerable attention due to their wide‐ranging applications in organic synthesis, material science, agrochemicals, and the pharmaceutical industry. Given the significant bioactivity and extensive applications of dithiocarbamates, the continuous pursuit of their efficient and diverse synthetic methods remains critical and urgent. Direct dithiocarbamation reactions can introduce ‐S‐C(S)NR2 group directly into parent molecules, providing shorter, greener, and more practical pathways for the synthesis of organodithiocarbamates. This article offers a comprehensive overview of the latest advancements in direct dithiocarbamation reactions, categorizing them based on the different sources of the ‐S‐C(S)NR2 group, with a particular emphasis on elucidating substrate scope and reaction mechanisms. Additionally, some synthetic limitations and applications of these methods are discussed. This review aims to provide the latest advancements in this field to both general readers and professional practitioners, inspiring innovative ideas for the synthesis of organosulfur compounds.

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Emerging Trends for the Direct Synthesis of Dithiocarbamates

He,

Zhou,

Liu

2024

Adv Synth Catal

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Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines

Halimehjani,

Noorakhtar,

Marjani

2024

Tetrahedron Letters

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Base-mediated synthesis of cyclic dithiocarbamates from 1-amino-3-chloropropan-2-ol derivatives and carbon disulfide

Abstract: An efficient method for the preparation of six-membered cyclic dithiocarbamates is described, in which triethylamine effectively promotes the reaction of 1-amino-3-chloropropan-2-ol derivatives with carbon disulfide. On the basis of the...

Cited by 2 publications

References 60 publications

Emerging Trends for the Direct Synthesis of Dithiocarbamates

Emerging Trends for the Direct Synthesis of Dithiocarbamates

Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines

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