An efficient eco-friendly catalyst-free three-component domino multicyclization for the synthesis of new spirobicyclic oxazolidinedione containing cyclopentenone moieties has been established by mixing amines, β-dicarbonyl compounds and ,'-dimethylalloxan in water at room temperature. This domino process involves multiple reactions such as enamination/aldol-like reaction/Stork enamine annulation/intramolecular cyclization under mild conditions.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9051567 | PMC |
http://dx.doi.org/10.1039/d0ra01699c | DOI Listing |
Chem Asian J
December 2024
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.
We present a comprehensive account of our efforts directed towards the synthesis of sacubitril, a neprilysin inhibitor used in combination with valsartan and marketed as Entresto™. Our initial approach to the formal synthesis of sacubitril employed a chiral pool strategy, utilizing (S)-pyroglutamic acid as a key building block and Cu(I)-mediated Csp-Csp cross-coupling as a key transformation. Further investigations led to the development of chiral amine transfer (CAT) reagents-based stereoselective synthesis.
View Article and Find Full Text PDFChemistry
November 2024
School of Physics and Information Technology, Shaanxi Normal University, Xi'an, 710119, China.
Polycyclic conjugated hydrocarbons have acquired increased interests recently because of their potential applications in electronic devices. On metal surfaces, the selective synthesis of four- and five-membered carbon rings remains challenging due to the presence of diverse reaction pathways. Here, utilizing the same precursor molecule, we successfully achieved substrate-controlled highly selective cycloaddition reactions towards four- and five-membered carbon rings.
View Article and Find Full Text PDFJ Org Chem
November 2024
School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China.
Isoindolones constitute a dominant structural class in synthetic and medicinal chemistry. In this research, an electrochemical reaction involving 2-alkynylbenzamides, inorganic sulfites, and alcohols was first established to provide sulfonyl ester-substituted 3-hydroxyisoindolinone derivatives in moderate to good yields with excellent functional group tolerance. When bulky aryl-substituted 2-alkynylbenzamides are utilized as substrates, sulfonyl ester-substituted 3-alkylideneisoindolinones can be selectively generated with good chemoselectivity.
View Article and Find Full Text PDFJ Org Chem
September 2024
Chemical Sciences & Technology Division, CSIR-North East Institute of Science & Technology, Jorhat 785006 Assam, India.
Herein, we report the Ag-catalyzed substrate-controlled interrupted radical pathways of the iminyl radical. The benzylic groups played a crucial role in pathway selection involving a series of dimerization and hydrolysis, a 1,5-H shift followed by cascade radical cyclization, and direct N-(sp)/aromatization reactions that provide access to diverse cyclic/acyclic ketones, quinolines, and phenanthridine derivatives. Contrary to previous reports, mechanistic investigations with high-resolution mass spectrometry analysis uncovered the involvement of rare azine, oxime, and β-functionalized vinyl azide intermediates.
View Article and Find Full Text PDFChem Sci
August 2024
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000 P. R. China
The radical-mediated difunctionalization of 1,3-enynes facilitates rapid access to structurally diverse allenes and dienes. Whereas, owing to the existence of multiple active sites in conjugated 1,3-enynes, regulating selectivity in difunctionalized addition a single transition-metal-catalyzed radical tandem process remains elusive. Herein, we disclose an intriguing protocol of substrate-controlled nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes with the assistance of sulfonyl chlorides and arylboronic acids.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!