Organocatalyzed Enantio- and Diastereoselective Domino [3+2]-Dipolar Cycloaddition: Synthesis of Chiral Pyrrorlo-thiazine-2-carbaldehydes and Dihydropyrrole-3-carbaldehydes

Published: Nov. 21, 2023

1,3-Dipolar cycloaddition of azomethine ylide and dipolarophile is an efficient method to construct N, S heterocycles such as thiazoles, 1,4-thiazines, their chiral polyhydro derivatives. Herein, we report a proline-derived organocatalytic enantioselective synthesis pyrrolo[1,2-d][1,4]thiazine-2-carbaldehydes using domino 1,3-dipolar cycloaddition/rearrangement sequence. This process yields fluorescent emissive, highly enantioenriched molecules with three contiguous stereogenic centers, having one quaternary center in single step, excellent yield, enantio- diastereoselectivity. strategy was extended the stereoselective one-pot novel tetrasubstituted dihydropyrrole-3-carbaldehydes via cycloaddition/rearrangement, followed by S-alkylation/base promoted ring-opening. A DFT study showed that formation hydropyrrolo-thiazole intermediate rate-determining step (TS7 E‡ = -28.49 kcal/mol) which responsible for pyrrolo[1,2-d][1,4]thiazine-2-carbaldehydes. Due high energy, hydropyrrolo-thiazole’s ring opens yield thiolate anion, C-N-bond rotation, intramolecular 1,2-addition ketone spontaneous protonation provides An in-silico pyrrolo-thiazine-2-carbaldehyde scaffolds have substantial anticancer activity respect B-Raf kinase, non-small cell line lung cancer.

Language: Английский

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Synthesis of Spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐ 5‐ones via 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol‐4‐ones

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(8)

Published: Feb. 22, 2024

Abstract Design of spirocyclic scaffolds, which are able for direct interaction with biological targets, is a developing trend in medicinal chemistry. In continuation the previous work on HIV‐1 inhibitors, synthetic approach towards spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐5‐ones via 1,3‐dipolar cycloaddition quinolinium ylides arylydeneimidazol‐4‐ones was outlined. Derivatives various substitution pattern were prepared 42–86 % yields. Use 2,2,2‐trifluoroethanol as solvent crucial successful preparation derivatives, its role sought prolonging lifetime cycloadducts.

Language: Английский

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A Base Promoted [3+2] Cycloaddition of Benzothiazolium Salts with Isoindigos to Synthesis N, S‐polyheterocyclic 3, 3′ Bispirooxindoles

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 26, 2024

Abstract A base promoted [3+2] cycloaddition of benzothiazolium salts with isoindigos has been developed, and a series novel N, S‐polyheterocyclic 3, 3′ bispirooxindoles four contiguous cycles two spiro quaternary stereocenters have successfully effectively prepared in good to excellent yields (up 99 %) under mild conditions.

Language: Английский

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The cycloaddition reaction of benzothiazolium ylides with α-cyanocinnamamides: the synthesis of structural analogs of inhibitors of HIV-1 post-integrational repair

Chemistry of Heterocyclic Compounds, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 30, 2024

Language: Английский

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