Synthesis, characterization and crystal structure of two polymorphs of trans N-benzyl-3,9,9-trimethyl-1,2,3,4,4a,9,9a,10-octahydroacridine

Acelas, Mauricio; Camargo, Hernando A.; Henao, J. A.; Kouznetsov, Vladímir V.; Bohórquez, Arnold R. Romero; Dugarte-Dugarte, Analio; Delgado, José Miguel Serrano; Delgado, Graciela Díaz de

doi:10.1016/j.molstruc.2020.128222

Cited by 2 publications

(2 citation statements)

References 34 publications

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“…A one-pot diastereoselective synthesis of new N -substituted octahydroacridines was successfully achieved by Kouznetsov et al. [ 113 , 114 ] via BiCl 3 -catalyzed intramolecular cationic imino-Diels–Alder reaction. The intermediate iminium ions were prepared in situ through condensation of N -protected anilines 342 and (±)-citronellal 38 under mild reaction conditions (Scheme 93 ).…”

Section: Intramolecular Povarov Reaction With Secondary Aminesmentioning

confidence: 99%

The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles

et al. 2023

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Nitrogen heterocycles are part of the structure of natural products and agents with important biological activity, such as antiviral, antibiotic, and antitumor drugs. For this reason, heterocyclic compounds are one of today’s most desirable synthetic targets and the Povarov reaction is a powerful synthetic tool for the construction of highly functionalized heterocyclic systems. This process involves an aromatic amine, a carbonyl compound, and an olefin or acetylene to give rise to the formation of a nitrogen-containing heterocycle. This review illustrates advances in the synthetic aspects of the intramolecular Povarov reaction for the construction of intricate nitrogen-containing polyheterocyclic compounds. This original review presents research done in this field, with references to important works by internationally relevant research groups on this current topic, covering the literature from 1992 to 2022. The intramolecular Povarov reactions are described here according to the key processes involved, using different combinations of aromatic or heteroaromatic amines, and aliphatic, aromatic, or heteroaromatic aldehydes. Some catalytic reactions promoted by transition metals are detailed, as well as the oxidative Povarov reaction and some asymmetric intramolecular Povarov processes.

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Section: Intramolecular Povarov Reaction With Secondary Aminesmentioning

confidence: 99%

The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles

et al. 2023

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“…Despite the potential applications as pharmacological models, only a few examples of OHA crystal structures have been reported. It must be mentioned that the structural features obtained from the crystallographic data have been of the utmost importance and have served to accurately describe the stereochemical preference of different OHA synthesis pathways (Li et al, 2018;Zaliznaya et al, 2016), illustrate molecular conformations (Frö hlich et al, 1994;Gan et al, 2000), and establish the effect of the reagent source (citronellal vs citronella essential oil) in the OHA crystal structure obtained via cationic Povarov reaction (Acelas et al, 2020).…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine

et al. 2021

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The title heterocyclic compound, C20H27N, has been prepared in good yield (72%) via a BiCl3-catalyzed cationic Povarov reaction between N-propargyl-4-methylaniline and (±)-citronellal. The X-ray single-crystal study indicates that the structure consists of molecules connected by C—H...π contacts to produce chains, which pack in a sandwich–herringbone fashion along the b-axis direction. Hirshfeld surface analysis indicates that H...H interactions dominate by contributing 79.1% to the total surface. Energy frameworks and DFT calculations indicate a major contribution of dispersive forces to the total interaction energy.

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Synthesis, characterization and crystal structure of two polymorphs of trans N-benzyl-3,9,9-trimethyl-1,2,3,4,4a,9,9a,10-octahydroacridine

Cited by 2 publications

References 34 publications

The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles

The Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles

Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine

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