Heterocyclodieneone photochemistry I. Photo-2-pyridone (2-aza-3-oxobicyclo[2.2.0]hex-5-ene)

Selms, Roy C. De; Schleigh, William R.

doi:10.1016/s0040-4039(01)94100-0

Cited by 28 publications

(8 citation statements)

References 8 publications

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“…The intramolecular electrocyclic [4π]-ring closure to 3-oxo-2-azabicyclo[2.2.0]-5-hexenes , and the [4 + 4]-photocycloaddition to dienes , represent two key photochemical reactions of 2-pyridones (pyridin-2(1 H )-ones) . In both reactions complex structures with at least two new stereogenic centers are formed from the prochiral heterocyclic substrate.…”

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confidence: 99%

“…The intramolecular [4π]-cyclization of the unsubstituted 2-pyridone 1a is known to proceed with low yields (15−21%). 1c,d We additionally employed for this study the 4-substituted pyridones 1b 15 and 1c 16 (Figure ), which cyclize more readily . Nonetheless, it was found experimentally that the velocity of their reaction significantly decreases with decreasing temperature.…”

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confidence: 99%

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Enantioselective Photochemical Reactions of 2-Pyridones in Solution

2001

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[reaction: see text] Two key photochemical reactions of prochiral 2-pyridones were studied in the presence of a chiral host. The [4 + 4]-photocycloaddition with cyclopentadiene (CpH) proceeded smoothly and with high enantioselectivity (84-87% ee). The absolute configuration of the endo-diastereoisomer was established by X-ray crystallography. The electrocyclic [4pi]-ring closure to 3-oxo-2-azabicyclo[2.2.0]-5-hexenes occurred with lower enantioselectivity (20-23% ee at -20 degrees C). The velocity of the latter reaction slowed significantly with decreasing temperature.

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Enantioselective Photochemical Reactions of 2-Pyridones in Solution

2001

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“…De Selms and Schleigh concluded that unsubstituted photoisomers, are relatively unstable. [82] However, substituted 2-pyridones led to relatively high degree of stability of the corresponding photopyridones. [81] In a more ex- Scheme 19. Photochemical electrocyclization N-methylpyridone 80.…”

Section: Electrocyclization Reactions With Pyridine Derivativesmentioning

confidence: 99%

Photochemical Rearrangements in Heterocyclic Chemistry

2019

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Heterocyclic compounds play an important role in many domains of chemistry. They are important structural elements in bioactive compounds. Photochemical reactions enable transformations of such compounds in a very convenient way. In many cases no chemical reagent is used. Members of one compound family can be transformed into members of another one. Three important types of photochemical rearrangements with heterocyclic compounds are discussed: Photochemical heteroatom isomerization involving heteroatoms and substituents, photochemical reactions involving hydrogen atom transfer (HAT) and photochemical electrocyclization.

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“…On the other hand, De Selms and Schleigh reported that upon irradiation in methanol, a range of substituted 2‐pyridones (some examples being the same substrates as studied by Paquette and Slomp) form mixtures of bicyclic lactams (resulting from 4‐π‐photocyclization) and dimeric products . Lactams 118 were reported to be stable indefinitely at room temperature, but to revert to 2‐pyridones upon heating above 100 °C.…”

Section: Heterocyclic 13‐diene Systemsmentioning

confidence: 99%

4‐π‐Photocyclization: Scope and Synthetic Applications

Coote

2019

Eur J Org Chem

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This minireview highlights the scope of 4‐π‐photocyclizations (photoinduced electrocyclizations that involve 4 pi electrons and generate bicyclic cyclobutenes from 1,3‐dienes), including an overview of the historical progressions as well as recent developments. A range of 1,3‐diene substrates is covered, including cycloheptatrienes, tropones, tropolones, cyclic 1,3‐dienes, 2‐pyrones, 2‐pyridones, pyrimidines, 1,2‐dihydropyridines, and 1,2‐dihydro‐pyridazines. The bicyclic cyclobutene products formed through the photocyclizations are highly versatile synthetic intermediates, and examples of the application of these building blocks in the context of synthetic methodology development, natural product synthesis, medicinal chemistry and materials chemistry are featured throughout.

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Heterocyclodieneone photochemistry I. Photo-2-pyridone (2-aza-3-oxobicyclo[2.2.0]hex-5-ene)

Cited by 28 publications

References 8 publications

Enantioselective Photochemical Reactions of 2-Pyridones in Solution

Enantioselective Photochemical Reactions of 2-Pyridones in Solution

Photochemical Rearrangements in Heterocyclic Chemistry

4‐π‐Photocyclization: Scope and Synthetic Applications

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