A facile synthesis of 3-substituted 5-oxo-1,2,4-thiadiazoles from amidoximes

Authors
Kohara, Y Kubo, K Imamiya, E Naka, T
Citation
Y. Kohara et al., A facile synthesis of 3-substituted 5-oxo-1,2,4-thiadiazoles from amidoximes, J HETERO CH, 37(6), 2000, pp. 1419-1423
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
6
Year of publication
2000
Pages
1419 - 1423
Database
ISI
SICI code
0022-152X(200011/12)37:6<1419:AFSO35>2.0.ZU;2-N
Abstract
The reaction of amidoximes 1 with 1,1(')-thiocarbonyldiimidazole (TCDI) fol lowed by treatment with silica gel or boron trifluoride diethyl etherate (B F3. OEt3) provided 3-substituted 4,5-dihydro-5-oxo-1,2,4-thiadiazoles 2 in moderate yields. The Lewis acids are considered to promote the rearrangemen t of the thioxocarbamate intermediates 5 to the thiolcarbamate intermediate s 7, which cyclize to afford 4,5-dihydro-5-oxo1,2,4-thiadiazoles 2.