Isothiocyanates (in situ) and sulfonyl chlorides in water for N-functionalization of bicyclic amidines: access to N-alkylated γ-/ω-lactam derivatized thiourea and sulfonamides

文献情報

出版日 2023-10-19

DOI 10.1039/D3OB01584J

インパクトファクター 3.876

著者

Pankaj Kumar, Aman Bhalla

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要旨

Herein, we showcase the potential of isothiocyanates generated in situ and aryl sulfonyl chlorides as electrophiles in water for N-functionalization of bicyclic amidines (DBN and DBU). This strategy provides complementary access to a range of thiouredosulfides, sulfonamides, aroylthioureas and amides derivativatized with distal γ- and ω-lactams. A novel sulfonyl chloride mediated formation of β-uredo sulfides has been achieved from β-isothiocyanato sulfides, removing the requirement for the harsh synthesis of unstable isocyanates. Mechanistic studies suggest a radical mechanism for the difunctionalization of alkenes, the efficacy of H2O in the ring opening of bicyclic amidines, and an oxygen source along with sulfonyl chloride as desulfurization agents for thiourea to afford urea derivatives.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

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