Expanding the Protecting Group Scope for the Carbonyl Olefin Metathesis Approach to 2,5-Dihydropyrroles

2021 ◽  
Author(s):  
Fabian Huck ◽  
Lorenzo Catti ◽  
Gian Lino Reber ◽  
Konrad Tiefenbacher
Keyword(s):  
Olefin Metathesis ◽  
Protecting Group

scholarly journals Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalysed Ring-Closing Carbonyl-Olefin Metathesis

2019 ◽  
Author(s):  
Yunfei Zhang ◽  
Jae Hun Sim ◽  
Samantha N. Macmillan ◽  
Tristan Lambert
Keyword(s):  
Nitrogen Atom ◽  
Olefin Metathesis ◽  
Catalytic Cycle ◽  
Protecting Group ◽  
Acid Labile

The synthesis of 1,2-dihydroquinolines by the hydrazine-catalysed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown, and the compatibility of these conditions with a range of additives is demonstrated. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnishes quinolines. In comparison to related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.

scholarly journals Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalysed Ring-Closing Carbonyl-Olefin Metathesis

2019 ◽  
Author(s):  
Yunfei Zhang ◽  
Jae Hun Sim ◽  
Samantha N. Macmillan ◽  
Tristan Lambert
Keyword(s):  
Nitrogen Atom ◽  
Olefin Metathesis ◽  
Catalytic Cycle ◽  
Protecting Group ◽  
Acid Labile

The synthesis of 1,2-dihydroquinolines by the hydrazine-catalysed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown, and the compatibility of these conditions with a range of additives is demonstrated. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnishes quinolines. In comparison to related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

Solid Supported Ruthenium Complexes for Olefin Metathesis

2013 ◽  
Vol 17 (22) ◽  
pp. 2592-2608 ◽  
Author(s):  
Fatma Hamad ◽  
Cheng Kai ◽  
Yuan Cai ◽  
Yu Xie ◽  
Yin Lu ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Ruthenium Complexes

Short Protecting Group-free Syntheses of CDE Synthon of Racemic Camptothecin

2020 ◽  
Vol 17 (7) ◽  
pp. 588-591
Author(s):  
Pingxuan Shao ◽  
Wei Lu ◽  
Lei Wang
Keyword(s):  
Total Synthesis ◽  
Future Development ◽  
Protecting Group ◽  
Short Route ◽  
The Future ◽  
Tricyclic Ketone

A practical and concise total synthesis of tricyclic ketone 7 (CDE ring), a valuable intermediate for the synthesis of racemic camptothecin and analogs, was described (8 chemical steps and 29% overall yield). The synthesis starts with two inexpensive, readily available materials and is operationally simple to perform. It is worth mentioning that the reported protecting group-free synthesis, with advantages of a short route, would be helpful for the future development of industry-scale syntheses of camptothecin-family alkaloids.

Fluoroquinolone-3-carboxamide Amino Acid Conjugates: Synthesis, Antibacterial Properties And Molecular Modeling Studies

2020 ◽  
Vol 17 (1) ◽  
pp. 71-84
Author(s):  
Riham M. Bokhtia ◽  
Siva S. Panda ◽  
Adel S. Girgis ◽  
Hitesh H. Honkanadavar ◽  
Tarek S. Ibrahim ◽  
...  
Keyword(s):  
Experimental Data ◽  
Antibacterial Activity ◽  
Amino Acid ◽  
Bacterial Infections ◽  
Antibacterial Agents ◽  
Antibacterial Properties ◽  
Computational Studies ◽  
Protecting Group ◽  
Amino Acid Conjugates ◽  
Molecular Modeling Studies

Background: Bacterial infections are considered as one of the major global health threats, so it is very essential to design and develop new antibacterial agents to overcome the drawbacks of existing antibacterial agents. Method: The aim of this work is to synthesize a series of new fluoroquinolone-3-carboxamide amino acid conjugates by molecular hybridization. We utilized benzotriazole chemistry to synthesize the desired hybrid conjugates. Result: All the conjugates were synthesized in good yields, characterized, evaluated for their antibacterial activity. The compounds were screened for their antibacterial activity using methods adapted from the Clinical and Laboratory Standards Institute. Synthesized conjugates were tested for activity against medically relevant pathogens; Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27856) Staphylococcus aureus (ATCC 25923) and Enterococcus faecalis (ATCC 19433). Conclusion: The observed antibacterial experimental data indicates the selectivity of our synthesized conjugates against E.Coli. The protecting group on amino acids decreases the antibacterial activity. The synthesized conjugates are non-toxic to the normal cell lines. The experimental data were supported by computational studies.

Olefin Metathesis over Mo–exchanged Zeolites: A Computational Review

2014 ◽  
Vol 4 (2) ◽  
pp. 216-230 ◽  
Author(s):  
Xin Li ◽  
Jing Guan ◽  
Gang Yang
Keyword(s):  
Olefin Metathesis
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