Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
The interaction of -dilithionaphthalenes with organic cyanides was studied. Instead of the expected -diimines, the reaction leads to the formation of three types of benzo[]isoquinolines. Treatment of unsubstituted 1,8-dilithionaphthalene with aromatic nitriles results in the formation of 1-amino-1,3-diaryl-1-benzo[]isoquinolines. In contrast, 4,5-dilithio-1,8-bis(dimethylamino)naphthalene gives an aromatic isoquinolonium cation via elimination of ammonia under the same condition. Upon treatment with -butylcyanide, both dilithionaphthalenes undergo a transformation to 1-amino-3,4-di--butyl-4-benzo[]isoquinolines. The observed reactivity was supported by quantum chemical calculations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.3c00035 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Aspartic acid residues in BBE-like enzymes from promote a function shift from oxidative cyclization to dehydrogenation.
Proc Natl Acad Sci U S A
August 2025
Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
Berberine bridge enzyme (BBE)-like enzymes catalyze various oxidative cyclization and dehydrogenation reactions in natural product biosynthesis, but the molecular mechanism underlying the selectivity remains unknown. Here, we elucidated the catalytic mechanism of BBE-like oxidases from involved in the oxidative cyclization and dehydrogenation of moracin C. X-ray crystal structures of a functionally promiscuous flavin adenine dinucleotide (FAD)-bound oxidase, MaDS1, with and without an oxidative dehydrogenation product were determined at 2.
View Article and Find Full Text PDFIn-Situ Reaction Monitoring and Mechanistic Studies by Mass Spectrometry: Heterogeneous Photocatalysis and Initial Contact Reaction.
Anal Chem
August 2025
State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P.R. China.
Elucidating reaction mechanisms in heterogeneous catalysis demands real-time tracking of transient species at the solid-liquid interface. To address limitations in directly probing surface processes with conventional mass spectrometry (MS), this work develops an innovative "in-source reaction" strategy by integrating the reactor with the electrospray ionization (ESI) source. Diverse catalysts (e.
View Article and Find Full Text PDFAcid-catalyzed, Three-component, Spontaneous Cascades of 1,3-Butadiynyl Propargylic Alcohols as a Route to Phthalan Derivatives.
ACS Catal
July 2025
Department of Chemistry, University of Minnesota, 207 Pleasant St., SE, Minneapolis, Minnesota 55455.
We have established an ambient temperature, one-pot, acid-catalyzed, three-component process involving in situ formation of a tetrayne or triyne that spontaneously cyclizes to a benzyne intermediate. This is rapidly captured to give a diverse range of polycyclic phthalan derivatives. Product structural diversity was enhanced by employing various combinations of alkyne substrates and benzyne trapping reagents.
View Article and Find Full Text PDFUndescribed indanomycin derivatives from ΔidmH mutant of Streptomyces antibioticus.
Eur J Med Chem
November 2025
School of Pharmacy, Naval Medical University, Shanghai, 200433, China; School of Pharmacy, Jiangxi University of Chinese Medicine, Nanchang, 330004, China; School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou, 350112, China. Electronic address:
Indanomycin represents a structurally distinctive polyether ionophore antibiotic featuring a pyrroloketoindane scaffold. The indane ring system, rare among natural products, is postulated to form through an enzymatic Diels-Alder cyclization. To obtain further knowledge of indanomycin biosynthesis, we chemically re-investigated the ΔidmH mutant of Streptomyces antibioticus.
View Article and Find Full Text PDFStructure and Mechanism of the Azomycin Biosynthetic Enzyme RohQ That Catalyzes a Spontaneous Cyclodehydration.
J Am Chem Soc
July 2025
Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada.
RohQ from the azomycin biosynthetic pathway catalyzes a spontaneous cyclodehydration to form 2-aminoimidazole. Here we report the structure and mechanism of RohQ and use a serendipitously bound imidazole to pinpoint active site residues. We propose that catalysis occurs at the dimeric interface using two key aspartic acid residues for proton transfer steps to accelerate 3 × 10-fold intramolecular cyclization of a guanidino group and aldehyde, releasing water.
View Article and Find Full Text PDF