[2+2]-Photocycloaddition of <i>N</i>-Benzylmaleimide to Alkenes As an Approach to Functional 3-Azabicyclo[3.2.0]heptanes

Skalenko, Yevhen; Druzhenko, Tetiana V.; Denisenko, Aleksandr V.; Samoilenko, Maryna; Dacenko, Oleksandr P.; Trofymchuk, Serhii; Grygorenko, Oleksandr O.; Tolmachev, Andrey A.; Mykhailiuk, Pavel K.

doi:10.1021/acs.joc.8b00077

Cited by 51 publications

(64 citation statements)

References 74 publications

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“…We then proceeded to evaluate several photosensitizers to establish which would provide optimal performance. Each of the evaluated photosensitizers demonstrated a substantial improvement in productivity as compared to the absence of any photosensitizer (Table , entry 4), with benzophenone and xanthone (entries 9 and 13, respectively) giving the best productivities and comparable yields. It was noted that the previously observed trends of higher productivities at low temperature and high pressure held true for reactions run in the presence of a photosensitizer (Table , entries 6 to 8).…”

Section: Resultsmentioning

confidence: 99%

Studies Toward the Scaling of Gas‐Liquid Photocycloadditions

et al. 2018

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The gas‐liquid biphasic photochemical [2+2] cycloaddition of maleic anhydride with ethylene was identified as a desirable strategy for the divergent synthesis of cyclobutane derivatives. To address the challenge of utilizing this transformation on a larger scale, studies toward the development of a stable process with sufficient productivity were undertaken. These studies revealed the importance of several reaction parameters to enhance both the gas solubility in solution and the efficient utilization of photons from various types of light sources.

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Section: Resultsmentioning

confidence: 99%

Studies Toward the Scaling of Gas‐Liquid Photocycloadditions

et al. 2018

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“…[232] Recent years have witnessedt he publication of numerouss ynthetic works on novel advanced buildingb locks for drug discovery,f ocusingm ainly on unusual bicyclic, spirocyclic, heteroaliphatic,o rh eteroaromatic compounds, especially those with fluorine atoms; selected examples are given in Figure 44. [233][234][235][236][237][238][239][240]…”

Section: Building Blocks For Drug Discoverymentioning

confidence: 99%

The Symbiotic Relationship Between Drug Discovery and Organic Chemistry

Grygorenko

Volochnyuk

Ryabukhin

et al. 2019

Chemistry A European J

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All pharmaceutical products contain organic molecules; the source may be a natural product or a fully synthetic molecule, or a combination of both. Thus, it follows that organic chemistry underpins both existing and upcoming pharmaceutical products. The reverse relationship has also affected organic synthesis, changing its landscape towards increasingly complex targets. This Review article sets out to give a concise appraisal of this symbiotic relationship between organic chemistry and drug discovery, along with a discussion of the design concepts and highlighting key milestones along the journey. In particular, criteria for a high‐quality compound library design enabling efficient virtual navigation of chemical space, as well as rise and fall of concepts for its synthetic exploration (such as combinatorial chemistry; diversity‐, biology‐, lead‐, or fragment‐oriented syntheses; and DNA‐encoded libraries) are critically surveyed.

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“…Synthesis of novel fused cyclobutane ring systems in this way would access new areas of chemical space, whilst retaining some of the conformational restriction often associated with successful drug molecules. Similar cyclobutane fused ring systems have previously been shown to have potential as bioisosteres for common building blocks in drug discovery …”

Section: Methodsmentioning

confidence: 93%

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

et al. 2019

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Cyclobutene alcohols undergo Prins cyclisations to generate single diastereomers of novel tricyclic heterocycles with five contiguous stereocentres. The reaction times are significantly shorter (ca. 15 min) than with traditional alkene substrates. Stereoselective aza‐Prins cyclisations of cyclobutene amine derivatives give fused aza‐heterocyclic scaffolds. Computational studies provide insight into the observed stereocontrol. The modular approach is flexible, enabling the introduction of a variety of functional groups (including amides, nitriles, alkynes, and arenes) into the sp3‐rich heterocyclic scaffolds.

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[2+2]-Photocycloaddition of N-Benzylmaleimide to Alkenes As an Approach to Functional 3-Azabicyclo[3.2.0]heptanes

Cited by 51 publications

References 74 publications

Studies Toward the Scaling of Gas‐Liquid Photocycloadditions

Studies Toward the Scaling of Gas‐Liquid Photocycloadditions

The Symbiotic Relationship Between Drug Discovery and Organic Chemistry

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

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