Two different pathways for the synthesis of annulated pyrido[3,4-]indoles are reported using metal-catalyzed cyclotrimerization reactions. A stepwise process using Rh(I)-catalysis in the final step of the synthesis and a multicomponent, tandem catalytic approach using Pd(0)-catalysis both lead to complex nitrogen-containing heterocycles in good yields. Substituent effects are investigated for both pathways, demonstrating that the Pd(0)-catalyzed approach is more sensitive to electron- withdrawing groups.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6519955 | PMC |
http://dx.doi.org/10.1016/j.tetlet.2018.10.050 | DOI Listing |
J Org Chem
January 2025
School of Science, China Pharmaceutical University, Nanjing 210009, P. R. China.
An -heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of alkynyl acylazoliums with benzothiazole derivatives has been developed for the divergent synthesis of axially chiral triaryl 2-pyranones and fused 2-pyridones. The regioselectivity of this protocol depends on the structure of benzothiazoles with three different nucleophilic centers. The obtained axially chiral frameworks represent a new class of arylheterocycle atropisomers, which may be potentially useful in medicinal chemistry.
View Article and Find Full Text PDFOrg Lett
January 2025
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
A copper-catalyzed [4 + 2] annulation protocol from readily available α,β-unsaturated ketoximes and dialkyl acetylenedicarboxylates has been achieved. The approach enables the expedient construction of a series of structurally new highly substituted pyridines with good functional group tolerance.
View Article and Find Full Text PDFChem Sci
January 2025
Institute of Chemistry, Academia Sinica 128 Academia Road, Section 2, Nankang Taipei 115201 Taiwan
Nanographenes and polycyclic aromatic hydrocarbons exhibit many intriguing physical properties and have potential applications across a range of scientific fields, including electronics, catalysis, and biomedicine. To accelerate the development of such applications, efficient and reliable methods for accessing functionalized analogs are required. Herein, we report the efficient synthesis of functionalized small nanographenes from readily available iodobiaryl and diarylacetylene derivatives a one-pot, multi-annulation sequence catalyzed by a single palladium catalyst.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry and Chemical Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640, China.
The chemoselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes with thioureas is reported. This protocol affords various attractive 6-fluoro-3,4-dihydropyrimidine-2(1)-thiones in high yields, features transition-metal free, mild conditions, efficient, is operationally simple and gram-scalable, tolerates diverse useful functional groups.
View Article and Find Full Text PDFChem Sci
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University Chongqing 401331 P. R. China
Reported herein is the first example of a ruthenium-catalyzed C-H activation/annulation of phenothiazine-3-carbaldehydes to construct structurally diverse pyrido[3,4-]phenothiazin-3-iums with dual-emission characteristics. Novel organic single-molecule white-light materials based on pyrido[3,4-]phenothiazin-3-iums with dual-emission and thermally activated delayed fluorescence (TADF) characteristics have been developed for the first time herein. Furthermore, the dual-emission molecule could be fabricated as water-dispersed NPs, which could be applied in two-channel emission intensity ratio imaging to observe the intercellular structure and can specifically target the cell membrane.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!