Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene N-arylpyrrolidine-diones

文献情報

出版日 2023-11-09

DOI 10.1039/D3OB01629C

インパクトファクター 3.876

著者

Pooja Dahiya, Anoop Yadav, Rama Krishna Peddinti

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要旨

Reactions of 3-benzylidene succinimides with 2-substituted 2-hydroxy-indane-1,3-diones and unsaturated pyrazolones are carried out under basic conditions to afford spirocyclized derivatives and Michael adducts, respectively, with high regio- and stereo-selectivities. The most notable aspect of the reaction is the ability of highly reactive benzylidene succinimide to act as both an electrophile and a nucleophile causing spirocyclization. The reaction proceeded under mild and metal-free conditions and products were isolated in good to high yields. The current strategy utilizes simple and easily accessible precursors, and provides functionally rich products of medicinal interest with two to four contiguous stereogenic centres and complete regioselectivity with excellent diastereoselectivity.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene N-arylpyrrolidine-diones

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