Acid-Catalyzed Condensation of Primary/Secondary Amines with 2-Oxo-2-aryl-N-arylethanethioamides: A Highly Regioselective Synthesis of α-Oxoamidines

In this letter, we present a synthesis of a-oxoamidines by the condensation of primary/secondary amines with N-aryl-α-oxothioamides catalyzed by benzoic acid in toluene at 80 °C. The required N-aryl-α-oxothioamide substrates were synthesized by the sodium hydride-induced condensation of aromatic ami...

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Bibliographic Details
Published in:Synlett 2024-11
Main Authors: Honnabandar, Kanaka Vijayashankar, Suresh, Rajaghatta N, Kavya, Kumar, Swaroop, Toreshettahally R, Rangappa, Kanchugarakoppal S, Mantelingu, Kempegowda
Format: Article
Language:English
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Summary:In this letter, we present a synthesis of a-oxoamidines by the condensation of primary/secondary amines with N-aryl-α-oxothioamides catalyzed by benzoic acid in toluene at 80 °C. The required N-aryl-α-oxothioamide substrates were synthesized by the sodium hydride-induced condensation of aromatic amines with α-oxodithioesters. The amines reacted with high regioselectivity toward thiocarbonyl groups over carbonyl groups to afford α-oxoamidines. The present method overcomes the limitations of previously reported methods.
ISSN:0936-5214
1437-2096
DOI:10.1055/a-2456-9704