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Synthesis of New 2,4-Diimino-1,3-thiazoles and the Structure Determination
Synthesis of New 2,4-Diimino-1,3-thiazoles and the Structure Determination
Journal of the Korean Chemical Society. 2003. Feb, 47(1): 38-42
  • Published : February 20, 2003
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Hahn, Hoh-Gyu
Lim, Chul-soo
Mah, Heduck

Abstract
For the purpose of developing new agrochemical fungicides, compound 2 possessing 1,3-thiazole scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazoline based on isosterism. The reaction of N-methylthiouea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazole 4 regioselectively, which was treated with phenyl isocyanates to give the corresponding 7 which is tautomer of 2. The structural assignment of 7 was confirmed by various spectra(<TEx>$^1H$ NMR, $^{13}C$ NMR, FT-IR, HRMS), and X-ray crystallographic data. Compound 8 which is a structural isomer of 7 was formed through thermodynamically unstable intermediate 2,4-diimino-1,3-thiazole 6.
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