An Automated Process for a Sequential Heterocycle/Multicomponent Reaction: Multistep Continuous Flow Synthesis of 5-(Thiazol-2-yl)-3,4-Dihydropyrimidin-2(1H)-ones

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J. Flow Chem. 2011, 1, 28-31

  • Nicholas Pagano, Ananda Herath and Nicholas D. P. Cosford*
  • Sanford-Burnham Medical Research Institute, 10901 N. Torrey Pines Rd., La Jolla, CA 92037, USA

This paper was performed on an Africa (now Asia) Synthesis Analysis and Liquid Handling flow chemistry system.

Abstract: The first example of a sequential heterocycle formation/multicomponent reaction using an automated continuous flow microreactor assembly is reported. Consecutive Hantzsch thiazole synthesis, deketalization, and Biginelli multicomponent reaction provides rapid and efficient access to highly functionalized, pharmacologically significant 5-(thiazol-2-yI)-3,4-dihydropyrimidin-2(1H)-ones without isolation of intermediates. These complex small molecules are generated in reaction times less than 15 min and in high yields (39-46%) over three continuous chemical steps.

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This paper was performed on an Africa (now Asia) Synthesis Analysis and Liquid Handling flow chemistry system.