In the title compound, C24H20N4, the azepine ring adopts a boat conformation. The dihedral angle between the benzene rings fused to the azepine ring is 49.40 (9)°. The triazole ring makes a dihedral angle of 77.88 (9)° with the terminal phenyl ring. In the crystal, mol-ecules are linked via C-H⋯π inter-actions and a parallel slipped π-π inter-action [centroid-centroid distance = 3.7324 (9), normal distance = 3.4060 (6) and slippage = 1.526 Å], forming a three-dimensional network.
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http://dx.doi.org/10.1107/S1600536813030547 | DOI Listing |
Acc Chem Res
January 2025
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.
View Article and Find Full Text PDFChemistry
December 2024
Organocatalysis Research Group, Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, 2. Magyar tudósok krt., H-1117, Budapest, Hungary.
A concise, bioinspired, and enantioselective synthesis of (-)-hunterine A, an odd 6/7/6/6/5 pentacyclic natural product, is described. The key step in the synthesis of this complex structure is an interim-template directed 6-exo selective epoxide ring-opening reaction, which is interwoven with a hydrolysis step of the indolenine hemiaminal template to create the unusual 7-membered azepine bridge motif. Our work not only refines the previously proposed biogenetic pathway, but also reveals the possible stereochemical prerequisite of the unique skeletal rearrangement, which provides a vantage point for understanding how (-)-hunterine A is likely to be generated in nature.
View Article and Find Full Text PDFChemistry
December 2024
School of Chemical Science and Technology & Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunmimg, 650500, PR China.
A curved nanographene, conceptually by insertion of nitrogen into a trapezoidal planar nanographene at the edge was synthesized by π-extension of the nitrogen-doped hexa-peri-hexabenzocoronene. This N-doped nanographene exhibited a π-electronic concave face containing a nonaromatic azepine ring in the middle with a size of 14.0 Å length and 4.
View Article and Find Full Text PDFBioorg Med Chem
October 2024
Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via Aldo Moro 2, 53100 Siena, Italy. Electronic address:
Riluzole, the first clinically approved treatment for amyotrophic lateral sclerosis (ALS), represents a successful example of a drug endowed with a multimodal mechanism of action. In recent years, different series of riluzole-based compounds have been reported, including several agents acting as Multi-Target-Directed Ligands (MTLDs) endowed with neuroprotective effects. Aiming at identical twin structures inspired by riluzole (2a-c), a synthetic procedure was planned, but the reactivity of the system took a different path, leading to the serendipitous isolation of benzo[b][1,4]thiazepines 3a-c and expanded intermediates N-cyano-benzo[b][1,4]thiazepines 4a-c, which were fully characterized.
View Article and Find Full Text PDFCell Chem Biol
August 2024
Department of Molecular, Cellular, & Developmental Biology, Yale University, New Haven, CT, USA; Department of Pharmacology, Yale University, New Haven, CT, USA; Department of Chemistry, Yale University, New Haven, CT, USA. Electronic address:
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