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Flow Synthesis of Ethyl Isocyanoacetate Enabling the Telescoped Synthesis of 1,2,4-Triazoles and Pyrrolo-[1,2-c]pyrimidines

Baumann, M.; Rodriguez Garcia, A.M.; Baxendale, I.R.

Flow Synthesis of Ethyl Isocyanoacetate Enabling the Telescoped Synthesis of 1,2,4-Triazoles and Pyrrolo-[1,2-c]pyrimidines Thumbnail


Authors

M. Baumann

A.M. Rodriguez Garcia



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.

Citation

Baumann, M., Rodriguez Garcia, A., & Baxendale, I. (2015). Flow Synthesis of Ethyl Isocyanoacetate Enabling the Telescoped Synthesis of 1,2,4-Triazoles and Pyrrolo-[1,2-c]pyrimidines. Organic and Biomolecular Chemistry, 14(13), 4231-4239. https://doi.org/10.1039/c5ob00245a

Journal Article Type Article
Acceptance Date Feb 26, 2015
Online Publication Date Feb 26, 2015
Publication Date Apr 14, 2015
Deposit Date Feb 26, 2015
Publicly Available Date Mar 29, 2024
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 14
Issue 13
Pages 4231-4239
DOI https://doi.org/10.1039/c5ob00245a

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