Synthesis of N‐Fused Indolines via Copper (II)‐Catalyzed Dearomatizing Cyclization of Indoles
Zhang, J., Xia, W., Huda, S., Ward, J. S., Rissanen, K., & Albrecht, M. (2021). Synthesis of N‐Fused Indolines via Copper (II)‐Catalyzed Dearomatizing Cyclization of Indoles. Advanced Synthesis and Catalysis, 363(12), 3121-3126. https://doi.org/10.1002/adsc.202100290
Published inAdvanced Synthesis and Catalysis
© 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.
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 bond in good yields. The tetracyclic 5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-ones are obtained in good to excellent yields (up to 99% yield) by using trifluoromethanesulfonic acid (TfOH) mediated N−Ts bond cleavage. The obtained compounds could be easily functionalized by simple synthetic methods.
Publication in research information system
MetadataShow full item record
Additional information about fundingJingyu Zhang gratefully acknowledges support by the Chinese Scholarship Council (CSC), Jas S. Ward the Finnish Cultural Foundation Central Fund (grant number 00201148) and Kari Rissanen the Alexander von Humboldt Foundation. (AvH research award) Open access funding enabled and organized by Projekt DEAL.
Showing items with similar title or keywords.
Savela, Risto; Shcherban, Nataliya D.; Melander, Marko M.; Bezverkhyy, Igor; Simakova, Irina L.; Långvik, Otto; Kholkina, Ekaterina; Schindler, Tamara; Krauβ, Annabelle; Honkala, Karoliina; Murzin, Dmitry Yu.; Leino, Reko (Royal Society of Chemistry, 2021)Selective hydrogenation of unsaturated imines over heterogeneous catalysts is an ecologically feasible and effective way to produce commercially valuable saturated imines and unsaturated amines under mild conditions, ...
1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions Schöbel, Jan-Hendrik; Elbers, Philipp; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten (Wiley-VCH Verlag, 2021)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 ...
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 ...
Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives Chen, Xiang-Yu; Xiong, Jia-Wen; Liu, Qiang; Li, Sun; Sheng, He; von Essen, Carolina; Rissanen, Kari; Enders, Dieter (Wiley-VCH., 2018)A strategy to control the switch between a non‐cycloaddition reaction and a cycloaddition reaction of enals, using N‐heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to γ‐amino‐acid ...
Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins : Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones Assoah, Benedicta; Riihonen, Vesa; Vale, João R.; Valkonen, Arto; Candeias, Nuno R. (MDPI, 2019)The preparation of unprecedented 6,12-disubstituted methanodibenzo[b,f][1,5]dioxocins from pyrrolidine catalyzed self-condensation of 2′-hydroxyacetophenones is herein described. This method provides easy access to this ...