A highly efficient and selective domino reaction producing valuable di- and tetrahydropyrrole-based skeletons from azidoethyl-substituted CH-acids and (thio)carbonyl compounds has been developed. By involving the additional functional groups in starting compounds into the domino reaction or postmodification of the primary reaction products, the simple construction of the pharmaceutically relevant three- and polycyclic azaheterocyclic scaffolds was demonstrated.
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http://dx.doi.org/10.1002/chem.201604056 | DOI Listing |
Org Lett
December 2024
Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya strasse, 6, 117198 Moscow, Russia.
Electrolysis of -alkynyl--(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia.
A domino approach towards β-carboline natural product taraxacine A and its analogues was developed. The main step relies on a silver(I) and base co-catalysed imidate-alkyne cyclization. The reaction tolerates primary and secondary alcohols, and various substitutions in the indole are possible.
View Article and Find Full Text PDFACS Omega
December 2024
School of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang 550014, P. R. China.
A transition metal-free domino Michael/S2/aromatization annulation of 2-pyridylacetates with bromonitroolefins has been developed. A wide range of substrates containing various substituted groups was compatible with the present methodology and afforded functionalized indolizines with moderate to excellent yield (up to 99% yield). In addition, the potential practicality of the method stood out through scale-up reactions and further transformations to other valuable compounds.
View Article and Find Full Text PDFJ Org Chem
December 2024
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.
View Article and Find Full Text PDFJ Org Chem
December 2024
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, P. R. China.
An effective and economical copper-catalyzed approach for the synthesis of phosphorylated 1-isochromenes is reported. This method is the first example of focus on ketone phosphonylation to establish a C-P bond and 6-- cyclization to construct a C-O bond between aryl- and alkyl-substituted alkynylketones and H-phosphinate esters, H-phosphites, and H-phosphine oxides, resulting in chemo- and regioselective phosphorylated 1-isochromenes with moderate to excellent yields under smooth reaction conditions.
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