Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines
- Marcus Baumann 1
- Antonio M. Rodriguez Garcia 1 2
- Ian R. Baxendale * 1
- 1 Department of Chemistry, Durham University, South Road, Durham, UK
- 2 Universidad de Castilla-La Mancha, Departamento de Química Orgánica, Facultad de Ciencias y Tecnologías Químicas, Avd. Camilo José Cela, 10, 13071 Ciudad Real, SpainRead the publication that featured this abstract
The efficient flow synthesis of important heterocyclic building blocks based on the 1,2,4-triazole and pyrrolo[1,2-c]pyrimidine scaffold has been achieved. Crucially, a telescoped continuous flow process was developed based on the reaction of N-formylglycine with triphosgene to deliver a stream of ethyl isocyanoacetate in situ, which subsequently yielded the desired heterocyclic entities in a telescoped reaction. Additionally, the functionalisation of the pyrrolo[1,2-c]pyrimidine core via subsequent SEAr reactions was studied revealing insight into a ‘halogen dance’ phenomenon associated with these medicinally relevant architectures.
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