A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2489202 | PMC |
http://dx.doi.org/10.1021/ol8008792 | DOI Listing |
Org Lett
January 2025
Department of Chemistry, Memorial University, St. John's, Newfoundland and Labrador A1B 3X7, Canada.
Organocatalytic, enantioselective decarboxylative Mannich reactions of α,β-unsaturated β'-ketoacids and isatin -Boc imines, to give the corresponding 3-carbamoyl-2-oxindole derivatives, were developed. Subsequent N-deprotection and diastereoselective, intramolecular, aza-Michael reaction of the free amine provides previously unreported spiro[indoline-3,2'-piperidine]-2,4'-diones.
View Article and Find Full Text PDFChem Biodivers
January 2025
Department of Chemistry, Faculty of Science, Taibah University, Medina Manora, Saudi Arabia.
In the current study, new pyranopyrazole analogs (9a-d and 10a-d) were synthesized through a one-pot condensation reaction of 2-arylacetohydrazide. The inhibitory abilities were investigated against the xanthine oxidase (XO) enzyme through experimental and molecular docking analyses. The synthesis studies were based on ultrasound-mediated condensation reactions of four-component containing 2-arylacetohydrazide, ethyl acetoacetate, indoline-2,3-dione, and ethyl 2-cyanoacetate/malononitrile in various solvents and catalysts to yield pyranopyrazole analogs (9a-d and 10a-d) in a short reaction time and remarkably favorable yields ranging from 79% to 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 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.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Pharmacy, Hebei Medical University, Shijiazhuang 050017, China.
We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!