5-Carbonyl-1,3-oxazine-2,4-diones from N-Cyanosulfoximines and Meldrum’s Acid Derivatives

Brosge, Felix; Kochs, Johanne,s Florian; Bregu, Mariela; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten

doi:10.1021/acs.orglett.0c02504

Final Draft

Katso/Avaa

420.3 Kb

Lataukset:

Show download details Hide download details

Brosge, F., Kochs, J., Bregu, M., Truong, K.-N., Rissanen, K., & Bolm, C. (2020). 5-Carbonyl-1,3-oxazine-2,4-diones from N-Cyanosulfoximines and Meldrum’s Acid Derivatives. Organic Letters, 22(16), 6667-6670. https://doi.org/10.1021/acs.orglett.0c02504

Julkaistu sarjassa

Organic Letters

Tekijät

Brosge, Felix |

Kochs, Johanne,s Florian |

Bregu, Mariela |

Truong, Khai-Nghi |

Rissanen, Kari |

Bolm, Carsten

Päivämäärä

2020

Oppiaine

Orgaaninen kemia Organic Chemistry

Tekijänoikeudet

At elevated temperatures, N-cyanosulfoximines react with Meldrum’s acid derivatives to give sulfoximines with N-bound 5-carbonyl-1,3-oxazine-2,4-dione groups. A representative product was characterized by single-crystal X-ray structure analysis. The product formation involves an unexpected molecular reorientation requiring several sequential bond-forming and -cleaving processes.

Julkaisija

American Chemical Society (ACS)

ISSN Hae Julkaisufoorumista

1523-7060

Lisenssi

Ellei muuten mainita, aineiston lisenssi on In Copyright

Näytetään aineistoja, joilla on samankaltainen nimeke tai asiasanat.

N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding

Schumacher, Christian; Fergen, Hannah; Puttreddy, Rakesh; Truong, Khai-Nghi; Rinesch, Torsten; Rissanen, Kari; Bolm, Carsten (Royal Society of Chemistry, 2020)

In the presence of KOH, NH-sulfoximines react with pentafluoropyridine to give N-(tetrafluoropyridyl)sulfoximines (NTFP-sulfoximines) in moderate to excellent yields. Either a solution-based or a superior solvent-free ...
Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades : Single Crystal X-ray and Chemical Structure Insights

Altowyan, Mezna Saleh; Soliman, Saied M.; Haukka, Matti; Al-Shaalan, Nora H.; Alkharboush, Aminah A.; Barakat, Assem (MDPI AG, 2022)

Hydrolysis/[3 + 2] cycloaddition/elimination cascades employed for the synthesis of unexpected tricyclic compound derived from isoquinoline. Reaction of ethylene derivative 1 with the isoquinoline ester iminium ion 2 in ...
Synthesis of Polycyclic Indolines utilizing a reduction/cyclization cascade reaction

Zhang, Jingyu; Xia, Wei; Qu, Meilin; Huda, Saskia; Ward, Jas; Rissanen, Kari; Albrecht, Markus (Wiley-VCH Verlag, 2021)

Subsequent reduction and dearomatizing cyclization reactions open up an entry into the synthesis of novel N-fused polycyclic indolines. The dearomatizing cyclization as key step of the sequence proceeds well with Cu(OTf)2 ...
Angular Regioselectivity in the Reactions of 2-Thioxopyrimidin-4-ones and Hydrazonoyl Chlorides : Synthesis of Novel Stereoisomeric Octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones

Said, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc (MDPI, 2020)

The regioselective synthesis of cis and trans stereoisomers of variously functionalized octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones was performed. The 2-thioxopyrimidin-4-ones used in the synthesis reacted with ...
A novel synthetic approach to pyran-2,4-dione scaffold production : microwave-assisted dimerization, cyclization, and expeditious regioselective conversion into β-enamino-pyran-2,4-diones

Sarhan, Ahmed A.M.; Haukka, Matti; Barakat, Assem; Boraei, Ahmed T.A. (Elsevier, 2020)

Here, we report a novel, green, simple, low-cost, and rapid methodology for the high-yield production of pyran-2,4-dione scaffolds under microwave irradiation. Regio- and stereoselective conversions of β-diketone systems ...