1314243-20-3Relevant academic research and scientific papers
N-Tosylhydrazone directed annulation via C-H/N-N bond activation in Ru(ii)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines
Deshmukh, Dewal S.,Bhanage, Bhalchandra M.
, p. 4864 - 4873 (2018)
A green and sustainable methodology for the synthesis of isoquinolines using Ru(ii)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annu
Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media
Deshmukh, Dewal S.,Gangwar, Neha,Bhanage, Bhalchandra M.
, p. 2919 - 2927 (2019/05/10)
Herein, we report an atom-efficient, rapid, green, and sustainable approach to synthesize isoquinolines and isoquinolinones using a homogeneous recyclable ruthenium catalyst in PEG Media assisted by microwave energy. Dibenzoylhydrazine was used for C–H/N–N activation reactions for the first time in combination with ketazine as oxidizing directing groups for annulation reactions with internal alkynes. The developed protocol is environmentally benign due to significantly shortened times with an easy extraction method, higher atom economy, external oxidant and silver or antimony salt free conditions, applicability to a gram scale synthesis, use of biodegradable solvent and wide substrate scope with higher product yields. Moreover, it is worth noting that the established methodology allowed reuse of the catalytic system for up to five successive runs with minimal loss in activity.
Cp*Co(iii)-catalyzed annulation of azines by C-H/N-N bond activation for the synthesis of isoquinolines
Deshmukh, Dewal S.,Yadav, Prashant A.,Bhanage, Bhalchandra M.
, p. 3489 - 3496 (2019/04/14)
Herein, an efficient, atom economic and external oxidant free approach has been disclosed for the synthesis of isoquinolines. Azines were employed for annulation reactions with alkynes via sequential C-H/N-N bond activation using an air-stable cobalt catalyst. The method takes advantage of the incorporation of both the nitrogen atoms of azines into the desired isoquinoline products, offering the highest atom economy. In addition, the developed protocol works under external oxidant as well as silver salt free conditions. Furthermore, the established methodology features a relatively broad substrate scope with high product yields and scalability up to the gram level.
Ruthenium-Catalyzed Annulation of N -Cbz Hydrazones via C-H/N-N Bond Activation for the Rapid Synthesis of Isoquinolines
Bhanage, Bhalchandra M.,Deshmukh, Dewal S.
, p. 2506 - 2514 (2019/06/08)
In this work, N -Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C-H/N-N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol
Synthesis of isoquinolines from α-aryl vinyl azides and internal alkynes by Rh-Cu bimetallic cooperation
Wang, Yi-Feng,Toh, Kah Kah,Lee, Jian-Yuan,Chiba, Shunsuke
supporting information; experimental part, p. 5927 - 5931 (2011/08/02)
Catalysts in a relay: A synthetic method for delivering highly substituted isoquinolines has been developed (see scheme; Cp =C5Me5, DMF=N,N-dimethylformamide, TEMPO=2,2,6,6-tetramethylpiperidine-1-oxyl). A preliminary mechanistic study showed that the rhodium and copper cooperate synergistically in the multistep sequence.
