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Synthesis of New 2,4-Diimino-1,3-thiazoles and the Structure Determination

새로운 2,4-Diimino-1,3-thiazoles 유도체의 합성과 구조 결정

  • Published : 2003.02.20

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($^1H$ 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.

Keywords

Isosterism;Agrochemical Fungicide

References

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Cited by

  1. Substituent effects of thiazoline derivatives for fungicidal activities against Magnaporthe grisea vol.99, pp.2, 2011, https://doi.org/10.1016/j.pestbp.2010.10.004