1,2,6-Thiadiazine 1-Oxides : Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides

Schöbel, Jan-Hendrik; Passia, Marco Thomas; Wolter, Nadja Anna; Puttreddy, Rakesh; Rissanen, Kari; Bolm, Carsten

doi:10.1021/acs.orglett.0c00666

Final Draft

Katso/Avaa

660.0 Kb

Lataukset:

Show download details Hide download details

Schöbel, J.-H., Passia, M. T., Wolter, N. A., Puttreddy, R., Rissanen, K., & Bolm, C. (2020). 1,2,6-Thiadiazine 1-Oxides : Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides. Organic Letters, 12(7), 2702-2706. https://doi.org/10.1021/acs.orglett.0c00666

Julkaistu sarjassa

Organic Letters

Tekijät

Schöbel, Jan-Hendrik |

Passia, Marco Thomas |

Wolter, Nadja Anna |

Puttreddy, Rakesh |

Rissanen, Kari |

Bolm, Carsten

Päivämäärä

2020

Oppiaine

Orgaaninen kemia Soveltavan kemian yksikkö Organic Chemistry The Unit of Applied Chemistry

Tekijänoikeudet

Unprecedented three-dimensional 1,2,6-thiadiazine 1-oxides have been prepared by an aza-Michael-addition/cyclization/condensation reaction sequence starting from sulfonimidamides and propargyl ketones. The products have been further functionalized by standard cross-coupling reactions, selective bromination of the heterocyclic ring, and conversion into a β-hydroxy substituted derivative. A representative product was characterized by single-crystal X-ray structure analysis.

Julkaisija

American Chemical Society

ISSN Hae Julkaisufoorumista

1523-7060

Rahoittaja(t)

Suomen Akatemia

Rahoitusohjelmat(t)

Tutkijatohtori, SA

Lisätietoja rahoituksesta

We thank the Alexander von Humboldt Foundation for support of K.R. (AvH research award), and we gratefully acknowledge Marcus Frings (RWTH Aachen University) for measuring the HPLC data. Further thanks go to Daniela Lutsch (RWTH Aachen University) for supporting practical experiments. Financial support from the Academy of Finland (RP Grant No. 298817) is also gratefully acknowledged.

Lisenssi

Ellei muuten mainita, aineiston lisenssi on In Copyright

Näytetään aineistoja, joilla on samankaltainen nimeke tai asiasanat.

Intregrating metallic wiring with three-dimensional polystyrene colloidal crystals using electron-beam lithography and three-dimensional laser lithography

Tian, Yaolan; Isotalo, Tero; Konttinen, Mikko P.; Li, Jiawei; Heiskanen, Samuli; Geng, Zhuoran; Maasilta, Ilari (IOP Publishing, 2017)

We demonstrate a method to fabricate narrow, down to a few micron wide metallic leads on top of a three-dimensional colloidal crystal self-assembled from polystyrene (PS) nanospheres of diameter 260 nm, using electron-beam ...
Convenient synthesis and X-ray determination of 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative activity

Tawfeek, Hendawy N.; Abdelmoez, Alshaimaa; Dahlous, Kholood A.; Youssif, Bahaa G. M.; Bräse, Stefan; Rissanen, Kari; Nieger, Martin; El-Sheref, Essmat M. (Royal Society of Chemistry (RSC), 2024)

A new series of 1,3,4-thiadiazin-3-ium bromide derivatives 9a–g were prepared as a six-member ring by interactions between 4-substituted thiosemicarbazides 8a–e and α-halo ketones 2a,b. The reaction was conducted using ...
Studies of two-dimensional and three-dimensional phononic crystal structures

Tian, Yolan (University of Jyväskylä, 2016)

This thesis focuses on studying phononic crystal structures. More specifically, it is aimed at fabrication and measurement of thermal properties of two-dimensional (2D) periodic microstructures and three-dimensional (3D) ...
N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions through α,β-Unsaturated Acyl Azolium Intermediates : Asymmetric Synthesis of Cyclopenta[c]chromenones

Liu, Qiang; Chen, Xiang-Yu; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter (Wiley, VCH Verlag GmbH & Co. KGaA, 2018)

An N‐heterocyclic carbene catalyzed domino sequence via α,β‐unsaturated acyl azolium intermediates has been developed. This strategy provides a convenient enantioselective route to functionalized tricyclic coumarin derivatives ...
Base-Controlled Regiospecific Mono-Benzylation/Allylation and Diallylation of 4-Aryl-5-indolyl-1,2,4-triazole-3-thione : Thio-Aza Allyl Rearrangement

Salama, Eid E.; Youssef, Mohamed F.; Boraei, Ahmed T., A.; Haukka, Matti; Soliman, Saied M.; Barakat, Assem; Sarhan, Ahmed A. M. (MDPI AG, 2023)

The regiospecific S-benzylation/allylation of two 4-aryl-5-indolyl-1,2,4-triazole-3-thione precursors was carried out using Et3N as a base. Allyl group migration from exocyclic sulfur to the triazole nitrogen (N3) was ...