1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions
Schöbel, J.-H., Elbers, P., Truong, K.-N., Rissanen, K., & Bolm, C. (2021). 1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions. Advanced Synthesis and Catalysis, 363(5), 1322-1329. https://doi.org/10.1002/adsc.202001505
Published inAdvanced Synthesis and Catalysis
© 2021 the Authors
Three‐dimensional aza‐analogues of 1,2‐benzothiazine 1,1‐dioxides have been prepared from sulfonimidamides. Two different protocols are presented. The first is a rhodium‐catalyzed annulation reaction with alpha‐sulfonyloxyketones leading to 4 unsubstituted benzothiazine derivatives. By selective bromination with NBS the heterocyclic ring can further be functionalized. In the second approach, an iridium catalyst is applied under solvent‐free mechanochemical conditions providing products with 3,4‐disubstituted thiazine rings from diazoketo esters and diazoketo sulfones.
Publication in research information system
MetadataShow full item record
Showing items with similar title or keywords.
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 ...
Riuttamäki, Saara; Laszkó, Gergely; Madarász, Ádam; Földes, Tamás; Pápai, Imre; Bannykh, Anton; Pihko, Petri M. (Wiley-VCH Verlag, 2022)We demonstrate herein the capacity of simple carboxylate salts – tetrametylammonium and tetramethylguanidinium pivalate – to act as catalysts in the isomerization of β,γ-unsaturated thioesters to α,β-unsaturated thioesters. ...
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 ...
Brosge, Felix; Kochs, Johanne,s Florian; Bregu, Mariela; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten (American Chemical Society (ACS), 2020)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 ...
Zhang, Jingyu; Xia, Wei; Huda, Saskia; Ward, Jas S.; Rissanen, Kari; Albrecht, Markus (Wiley, 2021)Herein, a copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is presented. Under mild reaction conditions, the cyclization proceeds to afford tetracyclic indolines by forming a new C−N ...