We have come across an unexpected reaction between electrophilic indoles and isoquinolinium methylides for accessing functionalized pyrrolo[2,1-a]isoquinolines. The reaction was found in general to yield the products in good yields. We also observed the formation of S-S-bridged bis-pyrrolo[2,1-a]isoquinolines from the reaction of 3-nitro benzothiophene and isoquinolinium methylides.
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http://dx.doi.org/10.1039/d1ob00005e | DOI Listing |
Org Lett
November 2024
School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, People's Republic of China.
Dearomative cycloadditions are valuable for efficiently generating three-dimensional molecular complexity. However, despite recent reports of cycloadditions of bicyclobutanes (BCBs) for the synthesis of aza-bicyclo[3.1.
View Article and Find Full Text PDFOrg Lett
June 2022
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
An array of chiral [1,2,4]triazino[5,4-]isoquinoline derivatives were obtained in excellent yields (up to 98%) and with excellent enantioselectivities (up to 99% ee) via a new highly asymmetric (3 + 3) cycloaddition reaction of diazo compounds and isoquinolinium methylides, with a bifunctional chiral phase-transfer catalyst (PTC). Density functional theory calculations show that PTC has a bridge role in the deprotonation/protonation process. The obtained products were transformed into densely functionalized polycyclic heterocompounds with multiple stereocenters.
View Article and Find Full Text PDFOrg Biomol Chem
March 2021
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, India. and Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India.
We have come across an unexpected reaction between electrophilic indoles and isoquinolinium methylides for accessing functionalized pyrrolo[2,1-a]isoquinolines. The reaction was found in general to yield the products in good yields. We also observed the formation of S-S-bridged bis-pyrrolo[2,1-a]isoquinolines from the reaction of 3-nitro benzothiophene and isoquinolinium methylides.
View Article and Find Full Text PDFChem Commun (Camb)
January 2015
Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany.
A phosphine-catalyzed dearomatizing [3+2] annulation of isoquinolinium methylides with allenoates or allenones yields highly functionalized pyrroloisoquinolines with high regioselectivity and in viable yields.
View Article and Find Full Text PDFJ Am Chem Soc
August 2013
Department of Chemistry and Biochemistry, University of Maryland, College Park, 20742, USA.
Convenient access to highly enantioenriched substituted quinolizidines has been achieved by chiral dirhodium(II) carboxylate-catalyzed dearomatizing formal [3 + 3]-cycloaddition of isoquinolinium/pyridinium methylides and enol diazoacetates. Coordination of Lewis basic methylides to dirhodium(II) prompts the rearrangement of the enol-carbene that is bound to dirhodium to produce a donor-acceptor cyclopropene. The donor-acceptor cyclopropene is in equilibrium with the dirhodium-bound enol-carbene and undergoes both enantioselective [3 + 3]-cycloaddition from the dirhodium-bound enol-carbene and diastereoselective [3 + 2]-cycloaddition by uncatalyzed reaction of the cyclopropene with isoquinolinium or pyridinium methylides.
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