Bicyclic 6-6 Systems with One Bridgehead (Ring Junction) Nitrogen Atom: No Extra Heteroatom

Avendaño, Carmen; Menéndez, J. Carlos

doi:10.1016/b978-008044992-0.01101-9

Cited by 5 publications

(3 citation statements)

References 195 publications

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“…However, taking into account the above-mentioned NOESY experiments, the relative configuration of compound 21 displaying 3 J 1,10b = 6.4 Hz was assigned as cis, and the configuration of the compound with 3 J 1,10b = 6.9 Hz as the trans isomer (Table 1). As it is known, the benzo[a]quinolizidine system can exist as interconvertible conformers due to the presence of a stereo- chemically mobile nitrogen atom [41]. Numbers of studies suggested that the preferred conformation of benzo[a]quinolizidines depended strongly on the type of substituents, the presence of stereocenters and their configuration [36,[41][42][43][44][45][46].…”

Section: Resultsmentioning

confidence: 99%

“…As it is known, the benzo[a]quinolizidine system can exist as interconvertible conformers due to the presence of a stereo- chemically mobile nitrogen atom [41]. Numbers of studies suggested that the preferred conformation of benzo[a]quinolizidines depended strongly on the type of substituents, the presence of stereocenters and their configuration [36,[41][42][43][44][45][46]. As for the 4-oxobenzo[a]quinolizidine derivatives, it should be noted that due to the planar amide fragment the interconversion of the different conformers could be largely suppressed.…”

Section: Resultsmentioning

confidence: 99%

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One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

Pashev

Burdzhiev

Stanoeva

2020

Beilstein J. Org. Chem.

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The Castagnoli–Cushman reaction of 3,4-dihydroisoquinolines with glutaric anhydride, its oxygen and sulfur analogues was investigated as a one-step approach to the benzo[a]quinolizidine system and its heterocyclic analogs. An extension towards the pyrrolo[2,1-a]isoquinoline system was achieved with the use of succinic anhydride. The results are evidence of an unexplored method for the access of the aforementioned tricyclic annelated systems incorporating a bridgehead nitrogen atom. The structures and relative configurations of the new compounds were established by means of 1D and 2D NMR techniques. The reactions between 1-methyldihydroisoquinoline and glutaric, diglycolic and succinic anhydrides yielded unexpected isoquinoline derivatives containing an exocyclic double bond. The compounds prepared bear the potential to become building blocks for future synthetic bioactive molecules.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

Pashev

Burdzhiev

Stanoeva

2020

Beilstein J. Org. Chem.

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“…Traditional methods usually require tedious reaction steps, and/or the use of structurally specific starting materials that are often difficult to access. 4,5 As such, the construction of bridged aza-tetracyclic scaffolds using readily available starting materials in a one-step manner would be a highly attractive way.…”

Section: Introductionmentioning

confidence: 99%

Iminyl radical-triggered relay annulation for the construction of bridged aza-tetracycles bearing four contiguous stereogenic centers

Jiang

Liu

et al. 2022

Chem. Sci.

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Chiral recognition in self‐complexes of diketopiperazine derivatives

Blanco

Alkorta

Rozas

et al. 2010

J of Physical Organic Chem

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The chiral discrimination in the self‐association of 2,5‐diketopiperazines derivatives has been studied using density functional theory (DFT) methods. Hence, clusters from dimers to tetramers have been considered. We have found a variety of linear and cyclic structures depending on the geometry of the monomers. In general, the heterochiral dimers (RR:SS or SS:RR) are more stable than the homochiral ones (RR:RR or SS:SS) with slight energetic differences. Nevertheless, most of the larger clusters (trimers and tetramers) show changes in stability, the homochiral cyclic structures being favored due to the better geometry of the hydrogen bond and/or the higher number of interactions. Some interesting correlations between the hydrogen bond geometrical descriptors and theoretical parameters obtained from the Natural Bond Orbital analysis (NBO), Natural energy decomposition analysis (NEDA), and the Atoms in Molecules theory (AIM) have been found. The chiral discrimination in the recognition process of these self‐complexes has been evaluated. In addition, evidence of cooperative effects has been observed. Copyright © 2010 John Wiley & Sons, Ltd.

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Bicyclic 6-6 Systems with One Bridgehead (Ring Junction) Nitrogen Atom: No Extra Heteroatom

Cited by 5 publications

References 195 publications

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

Iminyl radical-triggered relay annulation for the construction of bridged aza-tetracycles bearing four contiguous stereogenic centers

Chiral recognition in self‐complexes of diketopiperazine derivatives

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