![1H-Imidazo[4,5-c]pyridine-7-carboxylic acid structure](https://static.chemtradehub.com/structs/123/1234616-39-7-1344.webp "1H-Imidazo[4,5-c]pyridine-7-carboxylic acid structure")
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
Literature Information
Publication Date
2023-10-19
DOI
10.1039/D3OB01584J
Impact Factor
3.876
Authors
Pankaj Kumar, Aman Bhalla
View Original
Abstract
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.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
![[1-(5-Methyl-2-pyridinyl)-1H-pyrazol-4-yl]methanol structure](https://static.chemtradehub.com/structs/143/1439822-99-7-6cc9.webp "[1-(5-Methyl-2-pyridinyl)-1H-pyrazol-4-yl]methanol structure")
[1-(5-Methyl-2-pyridinyl)-1H-pyrazol-4-yl]methanol
CAS Number:
1439822-99-7
Molecular Formula:
C10H11N3O
Methyl 2-amino-4-(4-chlorophenyl)-5-pyrimidinecarboxylate
CAS Number:
1133115-56-6
Molecular Formula:
C12H10ClN3O2
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