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Synthesis 2024; 56(05): 787-794
DOI: 10.1055/a-2206-3750
DOI: 10.1055/a-2206-3750
paper
Sequential One-Pot Synthesis of β-Amino-γ-keto-malonates from Nitro-Substituted Donor–Acceptor Cyclopropanes
The authors thank Council of Scientific and Industrial Research (CSIR), India for financial support and Department of Science and Technology, Fund for Improvement of Science and Technology Infrastructure in Universities and Higher Educational Institutions (DST-FIST) for instrumentation facilities at the School of Chemistry, Bharathidasan University. S. S. thanks the University Grants Commission (UGC) for a BSR-RFSMS fellowship.
Abstract
A sequential one-pot procedure has been developed to access β-amino-γ-keto-malonates from nitro-substituted donor–acceptor cyclopropanes and four different nitrogen heterocycles. The reaction proceeds through in situ generation of aroylmethylidene malonates from 1-aryl-2-nitrocyclopropanes via Kornblum-type ring-opening oxidation using DMSO and subsequent aza-Michael addition with the nitrogen heterocycles. To prove the synthetic utility of the resulting products, one of them was transformed into a pyridazinone derivative.
Key words
β-aminomalonates - aroylmethylidene malonates - aza-Michael addition - donor–acceptor cyclopropanes - nitrogen heterocycles - one-pot synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2206-3750.
- Supporting Information
Publication History
Received: 26 July 2023
Accepted after revision: 08 November 2023
Accepted Manuscript online:
08 November 2023
Article published online:
11 December 2023
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