Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques

Abstract

An efficient and convenient solution-phase synthesis of a 1H-1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1H-1,2,4-triazole (1). MAOS was used for the synthesis of 5-amino-3-bromo-1,2,4-triazole analogs 3 and for their 3-aryl derivatives 4 via Suzuki–Miyaura coupling with polymer-supported catalyst. A microfluidic hydrogenation reactor integrated into an automated parallel synthesis platform was built and utilized for the reductive dehalogenation reactions providing 5-aminotriazoles (5).

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Correspondence to János Gerencsér.

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This manuscript is dedicated to Professor Árpád Furka on the occasion of his 80th birthday.

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Szommer, T., Lukács, A., Kovács, J. et al. Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques. Mol Divers 16, 81–90 (2012). https://doi.org/10.1007/s11030-012-9357-2

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Keywords

  • Microwave-assisted organic synthesis
  • Continuous-flow hydrogenation
  • 1H-1,2,4-triazole