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.

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: Aug 19, 2015
• 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
• Public URL: https://durham-repository.worktribe.com/output/1445080