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Issue 14, 2015
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Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines

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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.

Graphical abstract: Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines

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The article was received on 04 Feb 2015, accepted on 26 Feb 2015 and first published on 26 Feb 2015


Article type: Paper
DOI: 10.1039/C5OB00245A
Citation: Org. Biomol. Chem., 2015,13, 4231-4239
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    Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines

    M. Baumann, A. M. Rodriguez Garcia and I. R. Baxendale, Org. Biomol. Chem., 2015, 13, 4231
    DOI: 10.1039/C5OB00245A

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