An efficient synthetic protocol for novel indeno[1,2-a]fluorene derivatives was successfully developed by the base promoted domino reaction of 1,3-indanedione with 3-arylideneindolin-2-ones. The domino reaction in different solvents selectively gave carbamato- or amino-substituted indeno[1,2-a]fluorene in satisfactory yields. Additionally, a similar domino reaction of 1,3-indanediones with chalcones also gave polysubstituted indeno[1,2-a]fluorenes in high yields. The reaction mechanism is believed to proceed with base-promoted dimerization of 1,3-indanedione, Michael condensation, annulation, ring-opening of indolin-2-one and aromatization process.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c9ob01779h | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synergistic Pd/Ag-Catalyzed Domino Reaction: Access to Tetrahydropyrano[4,3-]pyran and Hexahydrofuro[2,3-]pyran.
Org Lett
January 2025
Department of Catalysis and Fine Chemicals, Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India.
We report the Pd-catalyzed and Ag-mediated temperature-dependent divergent synthesis of tetrahydropyrano[4,3-]pyran and hexahydrofuro[2,3-]pyran derivatives from a single substrate, alkynols. The reaction involves homocoupling of alkynols to form two C-O bonds and one C-C bond, resulting in tetrahydropyrano[4,3-]pyran cores at a high temperature (110 °C). Exposing tetrahydropyrano[4,3-]pyrans to a 200 W tungsten filament bulb yields tetrahydrofuro[2,3-]pyrans.
View Article and Find Full Text PDFUnexpected amine-triggered skeletal modification of fascaplysin and its derivatives: rapid access to δ,γ-biscarbolines.
Org Biomol Chem
January 2025
State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Guizhou Medical University, Guiyang 550014, China.
An unsuccessful attempt to directly construct alkaloid iheyamine A from a fascaplysin framework resulted in the discovery of a novel synthetic approach to alkylated δ,γ-biscarboline derivatives. With the easy-to-operate reaction conditions of this protocol, 18 alkylated biscarbolines have been prepared in moderate to good yields. An unexpected domino transformation was proposed to involve a pyridinium ring-opening/aza-electrocyclization/oxidative deformylation sequence.
View Article and Find Full Text PDFToward the Synthesis of Strychnos Alkaloids: Effective Construction of Fused Cyclohexane and Pyrrolidine Portion of the Strychnos Skeleton via Domino Intermolecular and Intramolecular S2 Cyclization.
Chem Pharm Bull (Tokyo)
January 2025
Graduate School of Integrated Basic Sciences, Nihon University, 3-25-40 Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan.
A method for preparing the fused cyclohexane and pyrrolidine portion of the strychnos skeleton has been developed using domino intermolecular and intramolecular S2 cyclization. Using this method, the formation of pyrrolidine proceeded smoothly with good yield without the E2 elimination product. This reaction condition is effective for synthesizing the fused cyclohexane and pyrrolidine portion of the strychnos skeleton.
View Article and Find Full Text PDFEnantioselective Heck/Tsuji-Trost reaction of flexible vinylic halides with 1,3-dienes.
Nat Commun
January 2025
College of Chemistry and Life Science, Advanced Institute of Materials Science, Changchun University of Technology, Changchun, P. R. China.
The enantioselective domino Heck/cross-coupling has emerged as a powerful tool in modern chemical synthesis for decades. Despite significant progress in relative rigid skeleton substrates, the implementation of asymmetric Heck/cross-coupling cascades of highly flexible haloalkene substrates remains a challenging and and long-standing goal. Here we report an efficient asymmetric domino Heck/Tsuji-Trost reaction of highly flexible vinylic halides with 1,3-dienes enabled by palladium catalysis.
View Article and Find Full Text PDFKnoevenagel-IMHDA and -IMSDA sequences for the synthesis of chiral condensed O,N-, S,N- and N-heterocycles.
RSC Adv
January 2025
Department of Organic Chemistry, University of Debrecen Egyetem Square 1 Debrecen 4032 Hungary
Domino Knoevenagel-cyclization reactions of styrene substrates, containing an -(-formyl)aryl subunit, were carried out with -substituted 2-cyanoacetamides to prepare tetrahydro-4-pyrano[3,4-]quinolone and hexahydrobenzo[]phenanthridine derivatives by competing IMHDA and IMSDA cyclization, respectively. The diastereoselective IMHDA step with α,β-unsaturated amide, thioamide, ester and ketone subunits as a heterodiene produced condensed chiral tetrahydropyran or thiopyran derivatives, which in the case of Meldrum's acid were reacted further with amine nucleophiles in a multistep domino sequence. In order to simplify the benzene-condensed tricyclic core of the targets and get access to hexahydro-1-pyrano[3,4-]pyridine derivatives, a truncated substrate was reacted with cyclic and acyclic active methylene reagents in diastereoselective Knoevenagel-IMHDA reactions to prepare novel condensed heterocyclic scaffolds.
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!