Beilstein J. Org. Chem.2018,14, 2266–2288, doi:10.3762/bjoc.14.202
of aromatic, vinyl, and heterocyclicamides. Thus, Ackermann and co-workers developed an inexpensive cobalt-catalyzed hydroarylation of isocyanates with (hetero)arenes 64 (Scheme 41) [100]. The reaction can tolerate a broad range of arenes and isocyanates, providing amide products 65 with notable
Beilstein J. Org. Chem.2017,13, 174–181, doi:10.3762/bjoc.13.20
, Faculty of Science, Masaryk University, Brno, Czech Republic 10.3762/bjoc.13.20 Abstract In this paper, we introduce a novel and convenient method for the transformation of heterocyclicamides into heteocyclic thioamides. A two-step approach was applied for this transformation: Firstly, we applied a
chlorination of the heterocyclicamides to afford the corresponding chloroheterocycles. Secondly, the chloroherocycles and N-cyclohexyl dithiocarbamate cyclohexylammonium salt were heated in chloroform for 12 h at 61 °C to afford heteocyclic thioamides in excellent yields.
Keywords: heterocyclicamides
; heterocyclic thioamides; N-cyclohexyl dithiocarbamate cyclohexylammonium salt; novel thiating agent; thiation; Introduction
Transforming heterocyclicamides into thioamides is an important task in organic synthesis. Earlier reports for this type of O/S conversions were achieved by several thiating reagents
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Graphical Abstract
Scheme 1:
Synthesis of N-cyclohexyl dithiocarbamate cyclohexylammonium salt (2).