Abstract
A series of tetrahydroquinoline derivatives were synthesized in good yields through Cu(OAc)2/t-butyl hydroperoxide (TBHP) assisted oxidative cyclization reaction. All the reactions were carried out in the aqueous medium at room temperature itself. In the oxidative cyclization reaction, dual functionalization of C(sp3)-H and C(sp2)-H bonds of the N,N-dimethylaniline was achieved in one-pot operation under mild reaction conditions. TBHP assisted synthesis of tetrahydroquinoline analogues was also successfully performed in the aqueous KCl medium in the absence of copper catalyst.
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Acknowledgements
Financial support from the Science and Engineering Research Board, DST-SERB (No. CRG/2021/001283) is gratefully acknowledged by S.S.G and P.S.K. Support of the DST under FIST programme (SR/FST/CS-I/2018/62) is gratefully acknowledged. All the authors thank the SASTRA Deemed University for providing lab space and NMR facility. P.S.K. thanks the financial assistance from DST through Young Scientist Initiative programme (SB/FT/CS-148/2013) and Water Technology Initiative program (WTI/2K16/215).
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Prasanna Kumari, S., Naveen, B., Suresh Kumar, P. et al. Cu/TBHP mediated tetrahydroquinoline synthesis in water via oxidative cyclization reaction. Chem. Pap. 77, 151–158 (2023). https://doi.org/10.1007/s11696-022-02462-z
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DOI: https://doi.org/10.1007/s11696-022-02462-z