Diastereoselective Assembly of Dispiro-cyclopentene-linked Bisoxindoles via Annulation Involving Isatylidene Malononitriles and Benzylamines

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Highly diastereoselective construction of the dispiro-bisoxindole skeleton by forming 5 new bonds and two rings.

Язык: Английский

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Synthetic Protocol for Pyrido[2,3-c]pyridazine and Pyrido[3,2-e][1,2]oxazine Scaffolds via a [4 + 2] Cycloaddition Reaction

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 14, 2025

Here, we revealed a convenient synthetic protocol for unique pyrido[2,3-c]pyridazine and pyrido[3,2-e][1,2]oxazine scaffolds with excellent regioselectvity diastereoselectivity. The functionalized pyrido[2,3-c] pyridazines were successfully synthesized via Cs2CO3-promoted [4 + 2] cycloaddition reaction of α-halogenated N-tosylhydrazones or N-acylhydrazones 5,6-unsubstituted 1,4-dihydropyridines under mild conditions. Additionally, the similar base-promoted α-chlorogenated oximes afforded pyrido[3,2-e][1,2]oxazines in satisfactory yields. features this included conditions, broad substrate scopes, high functional group tolerance, significant atomic economy.

Язык: Английский

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Construction of Unique Spiro[dibenzo[a,f]azulene-6,2′-indenes] via Unprecedented Annulation of ortho-C–H Bond of Benzylidene Group

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 14911 - 14927

Опубликована: Окт. 23, 2023

The domino reaction of alkyl and aryl isocyanides with two molecules 2-arylidene-1,3-indanediones in acetonitrile at 80 °C resulted unique functionalized spiro[dibenzo[a,f]azulene-6,2'-indenes] good yields, which the acted as different building blocks to construct polycyclic system. More importantly, unprecedented anticipation ortho-position benzylidene group form a novel dibenzo[a,f]azulene ring through formal [5 + 2] cycloaddition process was first observed. On other hand, DABCO-promoted afforded spiro[cyclopenta[a]-indene-2,2'-indene] derivatives.

Язык: Английский

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Synthesis of functionalized spiro[indanone-benzazepine] scaffolds via [4 + 3] annulation reaction of N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita−Baylis−Hillman carbonates

Tetrahedron, Год журнала: 2023, Номер 150, С. 133772 - 133772

Опубликована: Дек. 1, 2023

Язык: Английский

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Molecular Diversity of Base Promoted Annulation of MBH Carbonates of Isatins and Dialkyl But‐2‐ynedioates

ChemistrySelect, Год журнала: 2023, Номер 8(39)

Опубликована: Окт. 19, 2023

Abstract DABCO promoted one‐pot three‐component reaction of aromatic amines, dialkyl but‐2‐ynedioates and MBH nitriles isatins selectively afforded two diastereomeric spiro[indoline‐3,4′‐pyridines] in comparable yields. On the other hand, cyclization carbonates DCM at room temperature gave spiro[cyclopentane‐1,3′‐indoline] derivatives, while chloroform 70 °C resulted unique cyclopenta[ c ]quinolone derivatives with ring‐opening isatin moiety. A plausible mechanism was rationally proposed to explain formation different products.

Язык: Английский

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CAN Interceded Oxidative Coupling of β‐Dicarbonyl Compounds to 2‐Aryl/Heteroarylchromenes: A Regio‐ and Diastereoselective Synthesis of Tetrahydro‐benzofuro[3,2‐c]chromenones

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(12)

Опубликована: Фев. 21, 2024

Abstract A promising and useful method has been accomplished for regio‐ diastereoselective synthesis of tetrahydro‐benzofuro[3,2‐ c ]chromenones through ceric(IV) ammonium nitrate (CAN) mediated oxidative coupling cyclic/acyclic 1,3‐dicarbonyl compounds to 2‐aryl/heteroarylchromenes followed by a base assisted cyclization. The significant features the encircle easy accessibility starting materials, high air stability low toxicity oxidant CAN, product yield, operationally simple eco‐friendly reaction conditions. Trapping radical intermediate with scavenger TEMPO (detected LC–MS) from mixture proved that is process.

Язык: Английский

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Iodine promoted annulation reaction for selective construction of Spiro[indene-2,1′-pyrido[4,3-b]indole] and Benzo[5,6]pyrrolo[3′,2': 3,4]cyclohepta[1,2-b]indole

Tetrahedron, Год журнала: 2024, Номер 159, С. 134026 - 134026

Опубликована: Май 9, 2024

Язык: Английский

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Convenient Synthesis of Dihydrobenzofuran‐Fused Spirocyclopentane‐1,2‐Diindolinone Scaffolds

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

Опубликована: Окт. 17, 2024

Abstract The diverse functionalized dihydrobenzofuran‐fused spirocyclopentane‐1,2‐diindolin‐one scaffolds were conveniently synthesized by base promoted domino cyclization reaction of MBH (Morita‐Baylis‐Hillmann) carbonates isatins and 3‐( o ‐hydroxybenzylidene)indolin‐2‐ones. reactions maleimides formates with ‐hydroxybenzylidene)indolin‐2‐ones afforded polycyclic dispiro[indoline‐3,4′‐benzofuro[2′,3′:1,5]cyclopenta[1,2‐ c ]pyrrole‐5′,3′′‐indolines] dispiro[indoline‐3,1′‐cyclopenta[ b ]benzofuran‐2′,3′′‐indolines] in good yields high diastereoselectivity. More importantly, DMAP facilitated annulation nitriles selectively resulted dispiro[indoline‐3,1′‐cyclopentane‐2′,3′′‐indolines], while Cs 2 CO 3 gave relative configurations the various compounds clearly elucidated determination several single crystal structures.

Язык: Английский

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Construction of diverse spirooxindoles via a domino reaction of arylamines, but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(47), С. 9392 - 9397

Опубликована: Янв. 1, 2023

An iodine-promoted domino reaction of arylamines/benzylamines, dialkyl but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones showed very interesting molecular diversity. The in acetonitrile at 65 °C the presence 30% mmol I2 resulted spiro[indoline-3,1'-pyrido[4,3-b]indoles] satisfactory yields. When anilines without para-substituents were used reaction, a direct substitution hydroxyl group to 2-(phenylamino)maleate para-position aniline gave chain products good Additionally, similar reactions with benzylamines not only spiro[indoline-3,1'-pyrido[4,3-b]indoles], but also afforded spiro[indoline-3,1'-pyrano[4,3-b]indol]-2-ones lower A plausible annulation mechanism was rationally proposed for formation different kinds polycyclic compounds.

Язык: Английский

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Base Promoted Three‐component Reaction for Efficient Construction of Spiro[indoline‐3,3′‐quinoline]‐2,5′‐dione

ChemistrySelect, Год журнала: 2023, Номер 8(37)

Опубликована: Окт. 2, 2023

Abstract A convenient synthetic protocol for the construction of spiro[indoline‐3,3′‐quinoline]‐2,5′‐dione motifs was successfully developed by base promoted one‐pot three‐component reaction. In presence piperidine, reaction ammonium acetate, aromatic aldehydes and in situ generated 3‐isatyl 1,4‐dicarbonyl compounds, which were derived from mediated addition dimedone to 3‐methyleneoxindoles, resulted two diastereoisomers derivatives good yields with diastereoselectivity. The stereochemistry clearly elucidated isolation diastereomers determination several single crystal structures.

Язык: Английский

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