Date of Award
9-9-2023
Document Type
Thesis
School
School of Chemical & Biotechnology
Programme
Ph.D.-Doctoral of Philosophy
First Advisor
Dr.S.Selva Ganesan
Keywords
Copper Catalysis, Indole Fused Heterocyclic Compounds, Tetrahydroquinoline, Quinoline, Benzoylated Naphthol/ Phenol
Abstract
Copper catalyzed C-C, C-N/C-O bond formation reactions are a prominent tool to access diverse biologically relevant molecules. Herein, we present the copper- catalyzed diverse C-C/C-N(O) bond forming reactions. In Chapter-I (introduction), we briefly discussed the various copper mediated organic transformations with appropriate examples.
In Chapter II, we report a one-pot methodology for the vicinal aminoalkylation of naphthoquinone through a direct C(sp2)-H functionalization reaction. Through this method, readily available planar naphthoquinone substrates were transformed into three-dimensional molecular scaffolds through the formation of one C(sp2)-C(sp2) and two C(sp2)-N bonds. The indole fused nitrogen heterocyclic products were obtained in good yields. Apart from the heterocycle synthesis, Brønsted acid assisted diverse C-C and C-N bond forming reactions were also investigated with various nucleophiles.
In Chapter IIIa, a facile, room temperature chemooxidative Povarov-type cyclization reaction was carried out in the aqueous medium for the synthesis of diverse tetrahydroquinoline analogues. The products were obtained in good yields.
In Chapter IIIb, one-pot methodology was developed for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones from N,N-dimethylaniline. This methodology provides the desired pyrrolo[3,4-c]quinoline-1,3-dione products in good yields at room temperature itself.
In Chapter IV, A convenient methodology was developed for the synthesis of benzoylated naphthol and phenol derivatives through oxidative deamination reaction performed under aerobicreaction conditions. A synergistic combination of Cu(OTf)2 and Ag2O was used to convert the aminonaphthols and aminophenols to the corresponding benzoylated derivatives. The definite role of atmospheric oxygen to assist the reaction was proved by performing the reaction in the argon atmosphere.
Recommended Citation
S, Prasanna Kumari Ms, "Investigations on Copper Assisted Oxidative Transformations for the Construction of Diverse C-C/C-N(O) Bonds" (2023). Theses and Dissertations. 74.
https://knowledgeconnect.sastra.edu/theses/74