Organocatalytic Enantioselective [4+3]‐Cycloadditions of Azaoxyallyl Cations with 2‐Aminophenyl Enones

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(17), С. 4197 - 4203

Опубликована: Июль 12, 2021

Abstract The first organocatalytic asymmetric [4+3]‐cycloaddition of 2‐aminophenyl α,β‐unsaturated carbonyls with in situ generated azaoxyallyl cations was developed, and enantioenriched functionalized seven‐membered 1,4‐benzodiazepine‐3‐ones were obtained good yields excellent enantioselectivities. This approach also extended to the δ‐hydroxy carbonyls, affording 1,4‐oxazepanes one step under mild conditions. Several novel adducts demonstrated promising bioactivity prevention peripheral nerve degeneration. magnified image

Язык: Английский

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HFIP‐Mediated Decarboxylative [4+3]‐Annulation of Azaoxyallyl Cations with Isatoic Anhydride

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(17), С. 3594 - 3603

Опубликована: Май 15, 2020

Abstract The first example of a [4+3]‐annulation reaction between in situ‐generated azaoxyallyl cations and isatoic anhydride has been developed for the construction seven‐membered 1,4‐benzodiazepinediones moderate to good yields (up 91% yield). This annulation involves cascade decarboxylative addition hexafluoroisopropanol anhydride, cation, intramolecular substitution yield 1,4‐benzodiazepinediones. magnified image

Язык: Английский

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Organocatalytic Asymmetric [3 + 2]-Annulations of γ-Sulfonamido/γ-Hydroxy-α,β-Unsaturated Ketones with CyclicN-Sulfimines: Synthesis of Chiral Polyheterotricyclic Imidazolidines and Oxazolidines

The Journal of Organic Chemistry, Год журнала: 2022, Номер 88(2), С. 1113 - 1127

Опубликована: Дек. 29, 2022

The first organocatalytic asymmetric [3 + 2]-annulation of γ-sulfonamido-α,β-unsaturated ketones with cyclic N-sulfimines has been developed, and enantioenriched functionalized polyheterotricyclic imidazolidines were obtained in good yields excellent enantioselectivities. This approach was also extended to the γ-hydroxy-α,β-unsaturated ketones, affording oxazolidines. In addition, base-catalyzed 2]-annulations γ-sulfonamido/γ-hydroxy-α,β-unsaturated re-investigated under mild reaction conditions for synthesis racemic oxazolidines diastereoselectivities.

Язык: Английский

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Desymmetric [3+3] Cyclization of p-Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines

Organic Letters, Год журнала: 2024, Номер 26(9), С. 1770 - 1774

Опубликована: Фев. 14, 2024

General and efficient strategies for highly diastereoselective synthesis of divergent heterocyclic scaffolds through desymmetric [3+3] cycloaddition p-quinamines with 1,3-dipole surrogates hydroximoyl halides α-halohydroxamates have been developed. This synthetic protocol provided a variety architectures containing 1,2,4-oxadiazine hydroquinoxaline skeletons in good yields wide substrate scope.

Язык: Английский

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Base‐Promoted Cycloaddition of γ‐Hydroxy‐ and δ‐Hydroxy‐α,β‐Unsaturated Carbonyls with Azaoxyallyl Cations: Rapid Synthesis of N,O‐Heterocycles

European Journal of Organic Chemistry, Год журнала: 2020, Номер 2020(20), С. 3090 - 3100

Опубликована: Апрель 9, 2020

Metal‐free and environmentally friendly synthesis of morpholin‐3‐one 1,4‐oxazepan‐3‐one skeletons was achieved by the cycloaddition reaction alcohol‐tethered enones α‐halohydroxamates. This transformation proposed to proceed through addition hydroxyl group in enone an in‐situ generated azaoxyallyl cation followed intramolecular aza‐Michael‐type trapping. Accordingly, morpholin‐3‐ones 1,4‐oxazepan‐3‐ones could be from γ‐hydroxy δ‐hydroxy enones, respectively, a highly diastereoselective manner.

Язык: Английский

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Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(9), С. 6458 - 6466

Опубликована: Апрель 28, 2021

A one-pot synthetic method for indole/pyrrole-fused 1,4-diazepanone scaffolds has been developed. This involves a sequential amide coupling/intramolecular aza-Michael addition of 1H-indole/pyrrole-2-carboxylic acids with Morita–Baylis–Hillman-derived allylamines. The readily available starting materials, good stereoselectivity, and gram-scale synthesis make this valuable the construction highly substituted fused heterocycles containing moiety.

Язык: Английский

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Synthesis of Benzotriazepin-1-ones via Decarboxylative [4 + 3]-Annulation of Isatoic Anhydrides with Nitrile Imines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7290 - 7301

Опубликована: Май 17, 2023

A novel and streamlined approach to synthesizing benzotriazepin-1-ones has been developed through a hexafluoroisopropanol-promoted decarboxylative cascade reaction between isatoic anhydrides hydrazonoyl chloride. The [4 + 3] annulation of hexafluoroisopropyl 2-aminobenzoates with nitrile imines, generated in situ, is key feature this innovative reaction. This offered simple efficient method for broad range structurally intricate highly functional benzotriazepinones.

Язык: Английский

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Organocatalytic Asymmetric [4 + 2]-Cycloadditions of 2-Aminophenyl Enones with Isatin-Derived Ketimines: Diastereo- and Enantioselective Synthesis of Spirooxindole-Tetrahydroquinazolines

Organic Letters, Год журнала: 2023, Номер 26(1), С. 252 - 257

Опубликована: Дек. 26, 2023

A novel method for the enantioselective synthesis of spiro

Язык: Английский

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Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(4), С. 3546 - 3554

Опубликована: Фев. 4, 2021

The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up 99%). corresponding could be easily transformed into hydantoins via hydrolysis.

Язык: Английский

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Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(47)

Опубликована: Окт. 10, 2022

Abstract Aza‐oxyallyl cations, as proposed by Sheehan in the 1960s have garnered significant attention among synthetic organic community, owing to their diverse reactivity profile for constructing N‐scaffolds of biological interest. During its initial growth, aza‐oxyallyl cations were used effectively a 3‐unit synthon 1,3 dipoles create N‐heterocycles via cycloaddition reactions, wherein cation served electrophilic counterpart. Recently, new variations been reported, including usage 1,4 dipole domino and unique alkylating ability heteroatoms. This review article provides an update recent developments this area prevailing mechanistic insight.

Язык: Английский

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