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Synthesis 2024; 56(04): 677-685
DOI: 10.1055/a-2104-5943
DOI: 10.1055/a-2104-5943
special topic
Synthetic Development of Key Intermediates and Active Pharmaceutical Ingredients (APIs)
Base-Promoted 1,6-Aza-Michael Addition of Azauracils to para-Quinone Methides
This work was supported by the Science and Engineering Research Board (SERB) (CRG/2022/000470) and the Council of Scientific and Industrial Research, India (CSIR) (02(0426)/21/EMR-II). S.M. acknowledges the Department of Science and Technology, Ministry of Science and Technology, India (DST-FIST) (SR/FST/CS-II/2019/119(C)). R.D. thanks the University Grants Commission (UGC) for a fellowship.
Abstract
We report an efficient higher order conjugate addition of azauracils to substituted para-quinone methides (p-QMs) mediated by triethylamine to furnish hitherto unknown diarylmethane scaffolds through construction of a C–N bond. The protocol features mild conditions, high atom economy, and broad scope, and enables convenient access to biologically relevant new chemical entities (NCEs) comprised of p-QM and azauracil hybrids in good to excellent yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2104-5943.
- Supporting Information
Publication History
Received: 17 May 2023
Accepted after revision: 01 June 2023
Accepted Manuscript online:
01 June 2023
Article published online:
27 June 2023
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