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Synthesis 2018; 50(01): 139-145
DOI: 10.1055/s-0036-1590896
DOI: 10.1055/s-0036-1590896
paper
One-Pot Catalyst-Free Domino Condensation/Intramolecular 1,3-Dipolar Cycloaddition: Highly Stereoselective Access to Phosphadihydrocoumarin-Fused N,N-Bicyclic Pyrazolidin-3-ones
Further Information
Publication History
Received: 02 July 2017
Accepted after revision: 07 August 2017
Publication Date:
06 September 2017 (online)
Abstract
A concise, atom-economic, and highly regio/stereoselective synthetic strategy was developed for the construction of phosphorus- and nitrogen-fused polycyclic skeleton derivatives. The one-pot, two-step, catalyst-free domino condensation/intramolecular cycloaddition reaction of various substituted 2-(vinylphosphoryloxy)benzaldehydes with pyrazolidin-3-one took place at room temperature. Three new bonds (C–C, 2 × C–N) and two new nitrogen and phosphorus heterocycles were simultaneously constructed. The reaction is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.
Key words
catalyst-free - stereoselectivity - nitrogen and phosphorus heterocycles - polycycles - intramolecular cycloadditionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590896.
- Supporting Information
- CIF File
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