A Rh2(OAc)4-catalyzed diazo decomposition reaction of diazo esters with 2-aminophenyl ketones is reported. A series of 3-hydroxy-2,2,3-trisubstituted indolines are produced in good yields with excellent diastereoselectivities via an intramolecular aldol-type trapping of ammonium ylides with ketone units.
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http://dx.doi.org/10.1039/c3cc48067d | DOI Listing |
J Org Chem
January 2025
Chang-Kung Chuang Institute, Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, College of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf) as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.
View Article and Find Full Text PDFChem Biodivers
January 2025
Taibah University, Chemistry, Um alqara, Alula, SAUDI ARABIA.
In the current study, new pyranopyrazole analogues (9a-d and 10a-d) were synthesized through a one-pot condensation reaction of 2-arylacetohydrazide. The inhibitory abilities were investigated against the XO enzyme through experimental and molecular docking analyses. The synthesis studies were based on ultrasound-mediated condensation reactions of four-component systems containing 2-arylacetohydrazide, ethyl acetoacetate, indoline-2,3-dione, and ethyl 2-cyanoacetate/malononitrile in various solvents and catalysts to yield pyranopyrazole analogues (9a-d and 10a-d) in a short reaction time and remarkably favorable yields ranging from 79-92%.
View Article and Find Full Text PDFChemistry
January 2025
School of Pharmaceutical Sciences, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, Henan, China.
An unprecedented formal [1+5] cyclization of indoline-derived azadienes with 1,3,5-triazinanes has been realized, providing a facile access to biologically important indoline-spiro-hexahydropyrimidines with good to excellent yields (up to 99 % yield). Different from previous reports, this is the first study that indoline-derived azadienes could participate in cyclizations as one-atom synthons. This methodology is also distinguished by not involving any additive or catalyst, readily available starting materials, wide range of substrate applicability, operational simplicity and simultaneously reassembling two C-N and two C-C bonds in one-step reaction.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489, Berlin, Germany.
Here we disclose that spiropyrans are able to undergo dynamic covalent exchange via their corresponding merocyanine isomers. In the latter, the indolinium moieties can be exchanged by a Michael-type addition-elimination sequence, in which a methylene indoline attacks a merocyanine and subsequently the initial indoline fragment is cleaved. The rate and position of the exchange equilibrium strongly depend on the reaction conditions as well as the substitution pattern on the methylene indoline fragments.
View Article and Find Full Text PDFOrg Lett
January 2025
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China.
The cascade reaction of 3-diazo-2-sulfonyliminoindolines and -methoxymethyl--[(trimethylsilyl)methyl]benzylamines generates 2-sulfonylimino-1',3',4',6'-tetrahydro-2'-spiro[indoline-3,5'-pyrimidine] and spiro[indoline-3,3'-pyrrolidine] derivatives simultaneously under the catalysis of TFA and blue light irradiation. Their formation mechanisms were proposed on the basis of isotope-labeled experiments and HRMS analysis of the controlled experiment mixture, showing new reaction pathways. The current reaction provides a new strategy for the synthesis of biologically important spiro[indoline-3,3'-pyrrolidine]-2-one derivatives.
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