Heterocycles from cyclopropenones

Aly, Ashraf A.; Hassan, Alaa A.; Mostafa, Sara M.; Mohamed, Asmaa H.; Osman, Esraa M.; Nayl, A.A.

doi:10.1039/d2ra03011j

Cited by 6 publications

(3 citation statements)

References 129 publications

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“…While sufficiently stable in many biological contexts, CpO groups harbor significant ring strain that can be leveraged to drive covalent reactions [70–73] . CpO structures, for example, are subject to react with phosphine nucleophiles via Michael‐type reactions.…”

Section: Moving Beyond the Azide: Ligations With Cyclopropenonesmentioning

confidence: 99%

“…[70] While sufficiently stable in many biological contexts, CpO groups harbor significant ring strain that can be leveraged to drive covalent reactions. [70][71][72][73] CpO structures, for example, are subject to react with phosphine nucleophiles via Michael-type reactions. In a key demonstration, Hamada and Takizawa showed that diphenyl CpO reacts with triaryl phosphines to provide ketene-ylides; the ketenes were subsequently trapped by various nucleophiles in organic solvent.…”

Section: Moving Beyond the Azide: Ligations With Cyclopropenonesmentioning

confidence: 99%

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Bioorthogonal Phosphines: Then and Now

Dorn

Prescher

2022

Israel Journal of Chemistry

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Bioorthogonal chemistry traces its roots to a seminal report by Saxon and Bertozzi, who described a modified Staudinger reaction between organic azides and triaryl phosphines. This finding not only inspired several biological pursuits, but also launched an entire field of reaction discovery. Over the years, much effort has been directed at identifying alternative bioorthogonal transformations with organic azides; less work has focused on leveraging triaryl phosphines for new reaction development.The landscape has changed in recent years, with the generation of faster-reacting Staudinger probes and novel classes of bioorthogonal reagents. This perspective covers newly developed phosphine-based chemistries and their application in biological settings. We focus, in particular, on reactions with cyclopropenones and related analogs. These transformations feature unique mechanisms that are broadening the scope of bioorthogonal reactivity.

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Section: Moving Beyond the Azide: Ligations With Cyclopropenonesmentioning

confidence: 99%

Section: Moving Beyond the Azide: Ligations With Cyclopropenonesmentioning

confidence: 99%

Bioorthogonal Phosphines: Then and Now

Dorn

Prescher

2022

Israel Journal of Chemistry

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“…CPN has been theoretically, as well as experimentally investigated upon, along with its derivatives, over the past seven decades. − In particular, CPN plays its role as a tracer in nonequilibrium chemistry when interstellar acetylene and carbon-monoxide ices react under a cosmic shower . While CPN marks its presence in natural sources across the universe, some of its derivatives have demonstrated a wide range of biological activities and prominent medicinal qualities. Notably, Diphenylcyclopropenone (commercialized under “ Diphencyprone ”), has proven effective in treating Alopecia Areata , Autoimmune Disorders, Recalcitrant Warts, and also for In-transit Melanoma and a host of other ailments …”

Section: Introductionmentioning

confidence: 99%

Theoretical Appraisal of Cyclopropenone: Aggregation and Complexes with Water

et al. 2023

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Cyclopropenone (HCCOCH, “CPN”) is an exotic quasi-aromatic cyclic carbene that abounds in the interstellar medium (ISM). Astronomical observations suggest that (i) stagnate CPN exhibits a tendency to polymerize and that (ii) interactions may occur between CPN and water that is also ubiquitous in the ISM. In this light, density functional theory investigations reveal cooperative hydrogen bonding, which leads to stable polymeric conformations of (CPN) n , tracked up to n = 14. Stable agglomerations with water, however, constitute at best only two CPN and two water molecules, signifying that while CPN exhibits remarkable cooperativity for “cohesive” clustering via hydrogen bonding, this tendency is markedly diminished for “hetero”-interactions. Multifaceted data are employed to probe cogent molecular descriptors, such as structure and energetics of various conformers, vibrational spectroscopic response, molecular electrostatic potential (MESP), effective atomic charges: all these, in unison, describe the evolution of the characteristics upon cluster formation. Salient stretching frequency shifts, as well as charge redistribution gleaned from MESP morphology, have a direct bearing on variegated hydrogen bonding patterns: linear, nonlinear, as well as bifurcated. In particular, characteristic C–H, CO stretching, and O–H vibrations in the water complexes reveal a “softening” (downshift) of frequencies. While small conformers have markedly distinct MESP variations, the differences become less pronounced with incremental clustering, an effect substantiated by corresponding emergent atomic charges.

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Five-membered ring systems: pyrroles and benzo analogs

Lopchuk

2023

Progress in Heterocyclic Chemistry

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Heterocycles from cyclopropenones

Abstract: Great attention has been paid to cyclopropenones as they are present in many natural sources.

Cited by 6 publications

References 129 publications

Bioorthogonal Phosphines: Then and Now

Bioorthogonal Phosphines: Then and Now

Theoretical Appraisal of Cyclopropenone: Aggregation and Complexes with Water

Five-membered ring systems: pyrroles and benzo analogs

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