Publication: Synthesis of 1,2,4-Triazolo[4,3-a]pyrimidine Derivatives by Cyclocondensation of a 2-Thioxopyrimidin-4(3H)-one with Hydrazonoyl Halides
Synthesis of 1,2,4-Triazolo[4,3-a]pyrimidine Derivatives by Cyclocondensation of a 2-Thioxopyrimidin-4(3H)-one with Hydrazonoyl Halides
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Elwan, N. M., Awad, E. M., Hassaneen, H. M., Linden, A., & Heimgartner, H. (2003). Synthesis of 1,2,4-Triazolo[4,3-a]pyrimidine Derivatives by Cyclocondensation of a 2-Thioxopyrimidin-4(3H)-one with Hydrazonoyl Halides. Helvetica Chimica Acta, 86, 739–749. https://doi.org/10.1002/hlca.200390073
Abstract
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Abstract
The reaction of 1,2-dihydro-6-(phenylamino)-2-thioxopyrimidin-4(3H)one (16) with N-arylhydrazonoyl halides 15 in CHCl3 in the presence of Et3N under reflux afforded the corresponding 1,2,4-triazolo[4,3-a]pyrimidin-5-ones of type 20 in good yields (Scheme 3). The structure of one of the derivatives, 20d, has been established by X-ray crystallography. Conceivable reaction mechanisms are discussed in Schemes 3 and 4. The products of type 20 easily undergo reactions with electrophiles such as benzenediazonium chloride, chloroacetyl chlori
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- Elwan, Nehal M
- Awad, Enas M
- Hassaneen, Hamdi M
- Heimgartner, Heinz
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Elwan, N. M., Awad, E. M., Hassaneen, H. M., Linden, A., & Heimgartner, H. (2003). Synthesis of 1,2,4-Triazolo[4,3-a]pyrimidine Derivatives by Cyclocondensation of a 2-Thioxopyrimidin-4(3H)-one with Hydrazonoyl Halides. Helvetica Chimica Acta, 86, 739–749. https://doi.org/10.1002/hlca.200390073
