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, Spain
    Flow Synthesis and subsequent functionalisation

    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.

    Read the publication that featured this abstract

    Get in touch

    For more information on flow chemistry systems and services please use the contact methods below.

    Call us on +44 (0)1284 728659 or Email us

    Request a quote