5,10-Dihydroindeno[1,2-]indole has served as an important starting precursor for BARAC-fluor reagent in medicinal chemistry. Herein, an unprecedented -TsOH assisted intramolecular C2-arylation of NH-indoles via C(sp)-CN/C(sp)-H coupling, offering a series of 5,10-dihydroindeno[1,2-]indoles with moderate to good yields, has been showcased under redox-neutral conditions. Furthermore, successful scalability and synthetic applications highlight the practical nature of the method.
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http://dx.doi.org/10.1021/acs.orglett.4c02051 | DOI Listing |
Org Lett
August 2024
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, U.P., India.
5,10-Dihydroindeno[1,2-]indole has served as an important starting precursor for BARAC-fluor reagent in medicinal chemistry. Herein, an unprecedented -TsOH assisted intramolecular C2-arylation of NH-indoles via C(sp)-CN/C(sp)-H coupling, offering a series of 5,10-dihydroindeno[1,2-]indoles with moderate to good yields, has been showcased under redox-neutral conditions. Furthermore, successful scalability and synthetic applications highlight the practical nature of the method.
View Article and Find Full Text PDFOrg Biomol Chem
November 2022
School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India.
Palladium-catalysed and base-dependent intra-molecular -substitution and cyclisation strategies involving -indolyl-substituted aryl-sulfonamides for the rapid construction of 2-aryl indole and indole-fused six-membered sultams are described. The Pd(OAc)/PhP/EtN combination delivers indolyl C2 arylated motifs C(2)-N bond cleavage followed by C-C bond formation. In sharp contrast to this, the Pd(OAc)/PhP/KCO combination induced intramolecular-Heck cross-coupling affords polycyclic sultams exclusively.
View Article and Find Full Text PDFJ Org Chem
November 2014
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.
Pd-catalyzed direct C2 arylation and Cu-catalyzed direct one-pot alkynylation/intramolecular cyclization of azolium N-imides are reported. Various acetylenes, aryl iodides, and 1-alkyl substituents were examined. The mild protocol allows direct C2 arylation of azolium N-imides without the use of specialized reagents together with novel one-pot regioselective preparations of imidazole-pyrazolo and pyrazolo-1,2,4-triazole ring systems.
View Article and Find Full Text PDFJ Org Chem
July 2012
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India.
Regio- and stereoselective alkynylation of various N-heterocycles 1a-l using potassium and cesium salts in DMSO is described. Terminal alkynes 2a-k and internal alkynes 4a-f provided the kinetically stable Z-enamines 3a-l and 5a-i in good to excellent yields using KOH at 120 °C. Addition of heterocyclic amines to 1,3- and 1,4-diethynylbenzene 6a-b provided the mixture of E/Z isomers with KOH; however, with Cs(2)CO(3) selectively Z-isomers 7ab-db were obtained by the hydroamination at one triple bond.
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