Intramolecular Dehydrogenative Photocyclization of N-Phenyl-1-naphthamides

Organic Letters, Год журнала: 2024, Номер 26(25), С. 5364 - 5369

Опубликована: Июнь 14, 2024

Here, we explore a dehydrogenative 6π photocyclization method for

Язык: Английский

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Transforming an azaarene into the spine of fusedbicyclics via cycloaddition-induced scaffold hopping of 5-Hydroxypyrazoles

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Дек. 30, 2024

Skeleton editing for heteroarenes, especially pyrazoles, is challenging and remains scarce because these non-strained aromatics exhibit inert reactivities, making them relatively inactive performing a dearomatization/cleavage sequence. Here, we disclose cycloaddition-induced scaffold hopping of 5-hydroxypyrazoles to access the pyrazolopyridopyridazin-6-one skeleton through single-operation protocol. By converting five-membered aza-arene into five-unit spine 6/6 fused-bicyclic, this work unlocks ring-opening reactivity pyrazole core that involves formal C = N bond cleavage while retaining highly reactive N-N in resulting product. A [4 + 2] cycloaddition temporarily dearomatized 5-hydroxypyrrole with an situ generated aza-1,3-diene, followed by oxidative C-N cleavage, constitutes domino pathway. library pyrazolopyridopyridazin-6-ones, which are medicinally relevant nitrogen-atom-rich tricyclics, obtained efficiently from readily available materials.

Язык: Английский

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From an Azaarene to the Spine of Fused Bicyclics: Cycloaddition-Induced Scaffold Hopping of 5-Hydroxypyrazoles

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Июль 9, 2024

Skeleton editing for heteroarenes, especially pyrazoles, is challenging and remains scarce due to these non-strained aromatics feature inert reactivities therefore relatively inactive perform a dearomatization/cleavage sequence. Herein, we disclose cycloaddition-induced scaffold hopping of 5-hydroxypyrazoles access pyrazolopyridopyridazin-6-one skeleton in single-operation protocol. By converting five-membered azaarene into five-unit spine 6/6 fused-bicyclics, this work has unlocked new ring-opening reactivity pyrrole core that involves formal C = N bond cleavage while retaining the highly reactive N-N resulting product. A [4 + 2] cycloaddition temporary dearomatized 5-hydroxypyrrole with anin situgenerated aza-1,3-diene follow-up oxidative C-N accounted domino pathway. library pyrazolopyridopyridazin-6-one, which are medicinally relevant nitrogen-atom-rich tricyclics, was obtained efficiently from readily available materials.

Язык: Английский

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Divergent Assembly of Functionalized Pyrazolo[1,5‐a]pyridine Derivatives via [3+2] Cyclization of N‐Aminopyridinium Salts with Various Unsaturated Hydrocarbons

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 10, 2024

Comprehensive Summary Two reaction modes for metal‐free [3 + 2] cyclization of N ‐aminopyridinium derivatives with β ‐alkoxyvinyl trifluoromethylketones have been described through selective C—O or C—O/C—C bond cleavage. This strategy can also be extended to the enaminones and bromoalkynes. A broad range ‐aminopyridinium, ‐aminoquinolinium, ‐aminoisoquinolinium salts are well tolerated, enabling divergent synthesis trifluoroacylated, non‐substituted, acylated, brominated pyrazolo[1,5‐ a ]pyridine (62 examples).

Язык: Английский

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Visible Light Mediated Iron‐Catalyzed One‐Pot Synthesis of Chromenopyrroles from Benzyl Alcohols, 2‐Hydroxyacetophenones and Methyl/Ethyl Isocyanoacetate at Room Temperature

ChemistrySelect, Год журнала: 2024, Номер 9(37)

Опубликована: Сен. 30, 2024

Abstract An effective, facile, trivial, and one‐pot procedure for the synthesis of chromenopyrroles from benzyl alcohols, 2‐hydroxyacetophenones, methyl/ethyl isocyanoacetate at room temperature in presence visible light has been developed. The Ag salt plays an important role activation cyclization step. Air‐stable low‐cost Knölker iron complex utilized dehydrogenation primary alcohols that would typically require a higher temperature. established protocol is scalable extensive functional group tolerance, generating good to excellent yields

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 421 - 484

Опубликована: Янв. 1, 2024

Язык: Английский

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Cascade Annulation for Synthesizing Chromenopyrrolones from o-Hydroxyphenyl Enaminones and 2-Halo-N-alkyloxyacetamides

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 27, 2024

A cascade cyclization reaction comprising two halogenation reactions and a Michael addition was developed for the synthesis of chromeno[2,3-

Язык: Английский

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Iodine as Polarity-Reversal Catalyst: Synthesis of a Fused Heterocycle with Contiguous Stereocenters

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 20, 2024

We report an unconventional I

Язык: Английский

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