Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(31), С. 6243 - 6262

Опубликована: Янв. 1, 2023

This article reviews the recent applications of Morita–Baylis–Hillman and Rauhut–Currier adducts nitroalkenes. It also covers mechanistic aspects, including key intermediates reaction pathways.

Язык: Английский

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DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Molecules, Год журнала: 2023, Номер 28(7), С. 3002 - 3002

Опубликована: Март 28, 2023

Allylation of N-unsubstituted isatin N,N'-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence 1-10 mol% DABCO DCM at room temperature, rapidly gave N-allylated and N, β-diallylated imine 1,3-dipoles moderate to high yields. The reaction features mild conditions, easily practical operation, short times most cases. Furthermore, alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through [3+2] or [3+3]-cycloaddition maleimides Knoevenagel adducts.

Язык: Английский

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Visible Light‐Mediated Reactions of β‐Nitroalkenes

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 12(1)

Опубликована: Ноя. 17, 2022

Abstract Organic transformations using visible light‐mediated photoredox reactions received significant attention in the past several years. Recently, nitroalkenes have emerged as an excellent coupling partner reactions. Due to easy availability and diverse reactivity, methodologies are reported on photoredox‐mediated of attain different types alkenes heterocycles. Variety including denitrative reactions, addition cycloadditions, etc. reported. However, a review that focuses entirely this topic has not appeared yet. Considering synthetic potential these class we provide summary various developed for under light catalysis.

Язык: Английский

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Highly diastereoselective [3+3] cycloaddition of indolin-3-ones and nitroallylic acetates: Efficient access to polysubstituted dihydropyrano[3,2-b]indoles

Tetrahedron, Год журнала: 2023, Номер 133, С. 133275 - 133275

Опубликована: Янв. 20, 2023

Язык: Английский

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Synthesis of tetrahydrochromenes and dihydronaphthofurans via a cascade process of [3 + 3] and [3 + 2] annulation reactions: mechanistic insight for 6-endo-trig and 5-exo-trig cyclisation

RSC Advances, Год журнала: 2023, Номер 13(9), С. 5796 - 5803

Опубликована: Янв. 1, 2023

Substituted tetrahydrochromenes and dihydronaphthofurans are easily accessible by the treatment of β-tetralone with trans-β-nitro styrene derived Morita-Baylis-Hillman (MBH) acetates through a formal [3 + 3]/[3 2] annulation. The reaction proceeds cascade Michael/oxa-Michael pathway moderate to good yields. A DFT study was carried out account for formation corresponding six five-membered heterocycles via 6-endo-trig 5-exo-trig cyclization.

Язык: Английский

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Synthesis of uniquely substituted 4H-Chromeno[2,3-d] pyrimidin-2-one derivatives by l-Proline catalyzed green chemistry method

Journal of the Indian Chemical Society, Год журнала: 2022, Номер 100(1), С. 100862 - 100862

Опубликована: Дек. 27, 2022

Язык: Английский

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Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation

RSC Advances, Год журнала: 2023, Номер 13(39), С. 27456 - 27460

Опубликована: Янв. 1, 2023

AB 2 C type four component quadruple cascade reaction between MBH acetate, 1,3-indanedione and aldehydes via [1 + 1 3] annulation progressed through Knoevenagel/Michael/Michael/Michael sequence for the synthesis of b is-spirocyclohexane.

Язык: Английский

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