Efficient domino approaches for the synthesis of multifunctionalized tricyclic fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones have been established. The reaction pathways were controlled by varying enaminones with different substituted patterns to give a series of new fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones selectively. The complete anti diastereoselectivity was achieved for the first reaction.
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http://dx.doi.org/10.1021/ol203166c | DOI Listing |
Org Lett
December 2024
DFG Cluster of Excellence livMatS @FIT, Institute of Organic Chemistry, Albertstraße 21, 79104 Freiburg (Breisgau), Germany.
facile access to -heteroaryl-fused bis-BODIPY scaffolds has been developed. A BODIPY dimer with an α,α-amine linker serves as a starting material to obtain pyrrole- and pyridine-fused BODIPYs, either by direct oxidation or by oxidative condensation with an aldehyde building block. Both species mark antipodal conjugative coupling conditions that result in distinct spectral outcomes.
View Article and Find Full Text PDFPhytochemistry
December 2024
School of Pharmaceutical Science & Yunnan Provincial Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, 650500, China; Yunnan College of Modern Biomedical Industry, Kunming Medical University, Kunming, 650500, China. Electronic address:
Voagafries A-E, five undescribed monoterpenoid indole alkaloids (MIAs), were isolated from the stem bark of Voacanga africana. Voagafrie A (1) has a unique 6/5/5/6/6 spiral ring skeleton with an indolone-fused 9-oxo-3-aza-tricyclo[6,3,1,0]-12-alkane-10-carbonyllactone. Voagafrie B (2) is a rare 5,6-seco diazine scaffold, whereas voagafrie C (3) possesses an octahydropyrrolo[2,3-b] pyrrole-fused 2,8-diazabicyclo[3.
View Article and Find Full Text PDFACS Org Inorg Au
December 2024
Institute of Chemistry, Academia Sinica, Nankang, Taipei 115201, Taiwan.
J Org Chem
December 2024
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.
A cascade cyclization reaction comprising two halogenation reactions and a Michael addition was developed for the synthesis of chromeno[2,3-]pyrrole-3-ones . Additionally, another cascade cyclization reaction, which involves a halogenation reaction followed by two intramolecular Michael additions, was established for the synthesis of chromeno[2,3-]pyrrole-2-ones . Both types of compounds were synthesized from -hydroxyphenyl enaminones and 2-halo--alkyloxyacetamides through a process that facilitated the intramolecular formation of C-C, C-O, and C-N bonds to effectively establish two fused rings in a single operation.
View Article and Find Full Text PDFChemistry
November 2024
Institute of Organic Chemistry of Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Here we present a highly versatile synthetic strategy based on twofold 6π-electrocyclization accompanied with HBr elimination as a novel approach towards centrosymmetric multi-heteroatom-doped nanographenes build around an electron-rich 1,4-dihydropyrrolo[3,2-b]pyrrole core. A straightforward synthesis from readily available substrates offers a unique possibility of fusing the 1,4-dihydropyrrolo[3,2-b]pyrrole subunit not only with carbocyclic building blocks, such as electron-deficient phenanthrenes, chrysenes, or [4]helicenes, but also with heterocyclic systems, such as benzo[b]furan and 5-thiatruxene. The clear advantage of this strategy is that there is no requirement to assemble complex scaffolds possessing bromoaryl units since bromine atom is introduced by bromination of 1,4-dihydropyrrolo[3,2-b]pyrrole core which, because of its exceptionally electron-rich character, is straightforward reaction.
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