Three-Dimensional Heterocycles by 5-exo-dig Cyclizations of <i>S</i>-Methyl-<i>N</i>-ynonylsulfoximines

Ma, Ding; Kong, Deshen; Wang, Chenyang; Truong, Khai‐Nghi; Bolm, Carsten

doi:10.1021/acs.orglett.1c03041

Cited by 8 publications

(3 citation statements)

References 58 publications

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“…Sulfoximines play an important role in medicinal and crop protection chemistry . With the goal of expanding their structural diversity, we started a program to incorporate sulfoximidoyl groups into heterocyclic scaffolds, resulting in the introduction of a range of new protocols for the preparation of heterocycles such as benzothiazines, benzo[ c ]isothiazole 2-oxides, and several other related compounds …”

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confidence: 99%

A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes

Wang

Bolm

2023

Org. Lett.

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N-Trifluoroacetylated (N-TFA) sulfoximines react with 1-trifluoromethylstyrenes in a one-pot domino reaction to give fluorinated 5,6-dihydro-1,2-thiazine 1-oxides in good to high yields. The process involves three sequential reaction steps that can be characterized as (1) nucleophilic allylic substitution (S N 2′), (2) hydrolysis, and (3) intramolecular nucleophilic vinylic substitution (S N V). The products can further be modified by defluorination. The molecular structure of the resulting product was confirmed by X-ray crystallographic analysis.

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confidence: 99%

A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes

Wang

Bolm

2023

Org. Lett.

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“…The possible mechanistic rationale of this intramolecular cyclization protocol is as follows (Scheme ). , In the presence of Et 3 N, one of the protons on the S -methyl is deprotonated to form a carbanionic intermediate A . The C-nucleophile (carbanion) then attacks the more electrophilic keto-carbonyl group intramolecularly and forms the cyclic intermediate B .…”

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confidence: 99%

“…However, another less explored aspect of sulfoximine chemistry is the reactivity of the α-carbon attached to the sulfur in N -substituted sulfoximines. This reactivity is driven by the acidity of the hydrogen at the α-carbon, which in turn depends on the nature of the substituents on the nitrogen atom. , Utilizing this, a few reactions on sulfoximine functionalization have been reported; however, most of them require strong bases and harsh reaction conditions . Gais and co-workers have explored this approach as a part of their synthesis of sulfoximine-substituted allylic alcohols, wherein they have treated 2-butanone with N -substituted sulfoximines .…”

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Base-Promoted Synthesis of S-Arylisothiazolones via Intramolecular Dehydrative Cyclization of α-Keto-N-acylsulfoximines

Chakraborty,

Das,

Barik

et al. 2023

J. Org. Chem.

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A base (Et 3 N)-promoted synthesis of 1,4-diarylisothiazolones from α-keto-N-acylsulfoximines has been achieved. The reaction proceeds via α-hydrogen abstraction from sulfoximine, followed by an intramolecular nucleophilic attack at the keto carbonyl to form a tert-hydroxy isothiazolone intermediate. The 1,4-substituted isothiazolone is obtained after dehydration via an E1cB path. This one-pot synthesis of isothiazolinones has a broad substrate scope, has a high atom economy, and provides products with good yields. The ΔE LUMO−HOMO is calculated using Gaussian 16 at the B3LYP/6-31G(d,p) level of theory.

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Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper‐Catalyzed Cross‐Coupling Reactions with Elemental Sulfur

Ward

Rissanen

et al. 2023

Adv Synth Catal

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Copper-catalyzed cross-coupling reactions of α-bromoaryl NH-sulfoximines with elemental sulfur lead to benzo [d][1,3,2]dithiazole-1-oxides, which represent a new class of three-dimensional heterocycles. The reactions proceed under mild conditions showing good functional group and heterocycle tolerance. By imination/oxidation, the initial cross-coupling products can be converted to unprecedented cyclic sulfonimidamides derivatives. Furthermore, a seven-membered heterocycle was obtained by a ruthenium-catalyzed ring-expansion with ethyl propiolate.

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Three-Dimensional Heterocycles by 5-exo-dig Cyclizations of S-Methyl-N-ynonylsulfoximines

Abstract: Upon treatment with Cs2CO3, S-methyl-N-ynonylsulfoximines undergo 5-exo-dig cyclizations to give three-dimensional heterocycles. The reactions proceed at ambient temperature with a wide range of substrates affording the corresponding products in good to excellent yields.

Cited by 8 publications

References 58 publications

A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes

A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes

Base-Promoted Synthesis of S-Arylisothiazolones via Intramolecular Dehydrative Cyclization of α-Keto-N-acylsulfoximines

Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper‐Catalyzed Cross‐Coupling Reactions with Elemental Sulfur

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