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One-Pot Synthesis of -Fused Quinolone-4 Tetracyclic Scaffolds from 2,2-Disubstituted Indolin-3-ones.
ACS Omega
November 2024
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia.
A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly of complex (dihydro)indolo[1,2-]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation of 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones to the corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. The latter can either be isolated with good yields (75-96%) or, in the case of -nitroacetophenone, used for further base-assisted intramolecular SAr cyclization resulting in indoxyl-fused quinolone-4 hybrids (up to 95%).
View Article and Find Full Text PDFSynthesis of Acenaphthene Fused Dithiaporphyrin(3.1.1.1)s and N-Fused Triphyrin(3.1.1)s in One-Pot Condensation.
Chem Asian J
November 2024
Indian Institute of Technology, Powai, Mumbai, 400076, India.
Two different types of novel nonaromatic acenaphthene fused macrocycles such as acenaphthene fused dithiaporphyrin(3.1.1.
View Article and Find Full Text PDFMetal-free synthesis of N-fused quinazolino-quinazoline-diones as a RNA triple helix intercalator.
RSC Med Chem
October 2024
Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology Kolkata-700032 India
The development of chemical scaffolds that target highly conserved RNA received attention due to its significance in splicing, nuclear organization, and gene expression in disease progression pathways. Here, we synthesized a series of N-fused quinazolino-quinazoline-diones a PIDA-induced C-N coupling methodology to target . Interestingly, compound 2z binds to the UUG pocket of a RNA triple-helix through intercalation, evidenced from molecular docking studies, fluorescence-based assay and CD experiments.
View Article and Find Full Text PDFIr-Catalyzed Asymmetric Hydrogenation of -Fused Heteroarenes with High Nitrogen Density: An Access to Chiral 2,5-Disubstituted 5,6-Dihydropyrrolo[1,2-][1,2,4]triazolo[5,1-]pyrazines.
Org Lett
September 2024
Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, China.
A highly enantioselective Ir-catalyzed asymmetric hydrogenation of 2,5-disubstituted pyrrolo[1,2-][1,2,4]triazolo[5,1-]pyrazines containing four nitrogen atoms has been first realized. Under additive-free conditions, a variety of chiral 2,5-disubstituted 5,6-dihydropyrrolo[1,2-][1,2,4]triazolo[5,1-]pyrazines can be afforded in high yields (86-98%) with excellent enantioselectivities of up to 99% ee. This method provides a straightforward strategy for the efficient synthesis of chiral multinitrogen polyheterocyclic compounds.
View Article and Find Full Text PDFNovel convenient 2-step synthesis of pyrido[1,2-]indoles from pyrylium salts and -bromoanilines.
Org Biomol Chem
August 2024
A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninsky Prospect 29, Moscow, 119991, Russia.
A novel convenient 2-step synthesis of substituted pyrido[1,2-]indoles is developed starting from easily available pyrylium tetrafluoroborates and -bromoanilines. A conversion of the pyrylium tetrafluoroborates to pyridinium ones followed by their palladium catalyzed intramolecular cyclization allows the formation of 24 examples of N-fused heterocycles. A one-pot two-stage cyclization procedure was developed.
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