Tandem reactions of the yttrium() catalyzed ring-opening reaction of 2,2'-diester aziridines with 3-(2-isocyanoethyl)indoles and the subsequent Friedel-Crafts/Mannich/desulfonylation were reported. A series of polycyclic spiroindolines containing tetrahydro-β-carbolines were obtained in moderate to excellent yields (56-92%) in one step under mild reaction conditions. A possible catalytic mechanism was also proposed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d1cc04576h | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enantioselective Organocatalyzed Cascade Dearomatizing Spirocycloaddition Reactions of Indole-Ynones.
Org Lett
October 2024
Department of Applied Chemistry, Anhui Province Engineering Laboratory for Green Pesticide Development and Application, and Anhui Province Key Laboratory of Crop Integrated Pest Management, Anhui Agricultural University, 230036 Hefei, China.
An intramolecular organocatalytic cascade dearomatizing spirocycloaddition reaction of indole-ynone compounds containing -silyl-naphthol substituents has been developed with the use of a chiral bifunctional thiourea. This process was able to provide various structurally diverse polycyclic spiroindolines in high yields (up to 98%) with excellent stereoselectivities (>20:1 dr, up to 98% ee) involving the formation of carbonylvinylidene -quinone methide intermediates.
View Article and Find Full Text PDFCatalyst-Free Synthesis of Polycyclic Spiroindolines by Cascade Reaction of 3-(2-Isocyanoethyl)indoles with 1-Sulfonyl-1,2,3-triazoles.
J Org Chem
July 2023
School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China.
Article Synopsis
- A new method was developed that allows for the reaction of 3-(2-isocyanoethyl)indoles with 1-sulfonyl-1,2,3-triazoles without the need for a catalyst.
- This process, called dearomative spirocyclization, efficiently creates polycyclic indolines that contain a spiro-α-carboline structure.
- The reaction takes place in a single step through thermal conditions, yielding the desired compounds in moderate to high amounts.
Recent progress in the homogeneous gold-catalysed cycloisomerisation reactions.
Org Biomol Chem
April 2023
Department of Chemistry, Faculty of Science, University of Lucknow, Lucknow 226007, UP, India.
Article Synopsis
- Interest in gold-catalysed reactions has surged over the past 20 years due to their versatility and ability to activate various unsaturated groups.
- This review highlights gold-catalysed cycloisomerisation reactions of ynamides, diynes, and 1-enynes, which allow for the synthesis of complex polycyclic compounds in a single step.
- These reactions are particularly useful for creating various unique structures, such as fused spiro carbocycles and other complex ring systems.
Divergent Synthesis of Chromenoindoles and Spiroindolines via Domino Reaction of Indolyl-Substituted Isocyanides with Quinone Esters.
Org Lett
September 2022
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan 250014, P. R. China.
A dearomative spirocyclization of tryptamine-derived isocyanides with quinone esters is developed for the divergent synthesis of structurally complex chromeno[2,3-]indole and polycyclic spiroindoline scaffolds. This domino reaction features the formation and conversion of the six-membered dihydropyran ring with an amendable ,-aminal moiety.
View Article and Find Full Text PDFλ-Iodane/Lewis Acid Mediated Intramolecular Cross-Nucleophile Coupling of β-Amino Acrylates: Chemodivergent Syntheses of Indole Alkaloidal Frameworks.
Org Lett
July 2022
Department of Medicinal Chemistry, School of Pharmacy, Hebei Medical University, 361 East Zhongshan Road, Shijiazhuang 050017, P. R. China.
Herein, we report an unprecedented intramolecular cross-nucleophile coupling strategy of indole tethered β-amino acrylates using a catalyst system combining λ-iodanes and Lewis acids to achieve the chemodivergent synthesis of three unique alkaloid skeletons. It was worth noting that the acquisition of spiroindolenines and azepino[4,5-]indoles derivatives was switchable with choice of the Lewis acids. Moreover, the polycyclic spiroindolines containing a lactone fragment could also be accessed for the first time via cross-nucleophile coupling cascade intramolecular condensation sequence.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!