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

Wang, Xianliang; Rissanen, Kari; Bolm, Carsten

doi:10.1021/acs.orglett.3c00415

acceptedVersion

Katso/Avaa

461.9 Kb

Lataukset:

Show download details Hide download details

Wang, X., Rissanen, K., & Bolm, C. (2023). A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes. Organic Letters, 25(9), 1569-1572. https://doi.org/10.1021/acs.orglett.3c00415

Julkaistu sarjassa

Organic Letters

Tekijät

Wang, Xianliang |

Rissanen, Kari |

Bolm, Carsten

Päivämäärä

2023

Oppiaine

Orgaaninen kemia Organic Chemistry

Tekijänoikeudet

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 (SN2′), (2) hydrolysis, and (3) intramolecular nucleophilic vinylic substitution (SNV). The products can further be modified by defluorination. The molecular structure of the resulting product was confirmed by X-ray crystallographic analysis.

Julkaisija

American Chemical Society (ACS)

ISSN Hae Julkaisufoorumista

1523-7060

Lisätietoja rahoituksesta

The authors are grateful to the China Scholarship Council (CSC) for a predoctoral fellowship for X.W., and the authors acknowledge the Alexander von Humboldt Foundation for support of K.R. (AvH research award).

Lisenssi

Ellei muuten mainita, aineiston lisenssi on In Copyright

Näytetään aineistoja, joilla on samankaltainen nimeke tai asiasanat.

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

Wu, Peng; Ward, Jas S.; Rissanen, Kari; Bolm, Carsten (Wiley, 2023)

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 ...
Acetic Acid Mediated for One-Pot Synthesis of Novel Pyrazolyl s-Triazine Derivatives for the Targeted Therapy of Triple-Negative Breast Tumor Cells (MDA-MB-231) via EGFR/PI3K/AKT/mTOR Signaling Cascades

Shawish, Ihab; Barakat, Assem; Aldalbahi, Ali; Alshaer, Walhan; Daoud, Fadwa; Alqudah, Dana A.; Al Zoubi, Mazhar; Hatmal, Ma’mon M.; Nafie, Mohamed S.; Haukka, Matti; Sharma, Anamika; de la Torre, Beatriz G.; Albericio, Fernando; El-Faham, Ayman (MDPI AG, 2022)

Here, we described the synthesis of novel pyrazole-s-triazine derivatives via an easy one-pot procedure for the reaction of β-dicarbonyl compounds (ethylacetoacetate, 5,5-dimethyl-1,3-cyclohexadione or 1,3-cyclohexadionone) ...
Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Derivatives : X-ray Single Crystal Structure and Hirshfeld Analyses

Boraei, Ahmed T. A.; Haukka, Matti; Sopaih, Manar; Al-Majid, Abdullah Mohammed; Soliman, Saied M.; Barakat, Assem; Sarhan, Ahmed A. M. (MDPI AG, 2022)

A straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tet ...
Synthesis of Benzo[e][1,4,3]oxathiazin-3-one 1-Oxides from NH-S-(2-Hydroxyaryl)sulfoximines

Periasamy, Kiruthika; van Bonn, Pit; Tschekorsky Orloff, Runa; Völcker, Nils; Lu, Qiulan; Rissanen, Kari; Bolm, Carsten (American Chemical Society (ACS), 2024)

Cyclizations of NH-S-(2-hydroxyaryl)sulfoximines with 1,1′-carbonyldiimidazol (CDI) give unprecedented benzo[e][1,4,3]oxathiazin-3-one 1-oxides in good yields. The standard synthetic protocol involves the use of DCE at an ...
A Copper‐Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine‐1‐oxides

Hommelsheim, Renè; Bausch, Sandra; Selvakumar, Arjuna; Amer, Mostafa M.; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten (Wiley-VCH Verlag, 2023)

Copper(I)-catalyzed domino reactions of 2-azido sulfoximines with 1-iodoalkynes yield fused triazolyl-containing benzothiadiazine-1-oxides. The protocol features the synthesis of two fused heterocyclic rings in one step ...