- Construction of Functionalized Azapolycyclic Architectures via Formal Amide Insertion at a Low Catalyst Loading of Copper Trifluoroacetylacetonate
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A formal amide insertion reaction for the synthesis of nitrogen-bridged polycyclic frameworks with diverse functionalities was developed using a sustainable copper catalyst as an advantageous alternative to precious rhodium catalysts. The remarkable feature of this methodology is the amount of catalyst loading (0.05 mol%). The optimized reaction conditions enable access to aromatic ring-fused 8-azabicyclo[3.2.1]octane, 9-azabicyclo[3.3.1]nonane, and 6-azabicyclo[3.2.2]nonane derivatives in moderate to excellent yields. (Figure presented.).
- Harada, Shingo,Kato, Ryosuke,Nemoto, Tetsuhiro
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- Iron-Promoted Reductive Ring-Opening and Isomerization Reactions of C4-Alkynylisoxazoles Leading to 2-Alkynylenaminones and Polysubstituted Furans
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A new iron(III)-promoted reductive ring-opening and isomerization reactions of C4-alkynylisoxazoles in the oxidized N-methylpyrrolidone (NMP*) was reported. By changing the substituents at the C3 and C5 position of the isoxazole ring, the reaction selecti
- Yang, Wen,Chen, Yu,Yao, Yongqi,Lin, Qifu,Yang, Dingqiao
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p. 5634 - 5642
(2019/11/26)
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- One-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-Diels-Alder reactions of in situ generated N-arylimines and cyclic enamides
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An efficient synthesis of hexahydropyrrolo[3,2-c]quinolin-2-ones and hexahydropyridino[3,2-c]quinolin-2-ones has been developed in moderate to high yields by one-pot two-step aza-Diels-Alder reactions of N-arylimines, formed in situ from anilines and benz
- Zhang, Wei,Zhang, Wenxue,Dai, Yisi,Wang, Xuerui
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supporting information; experimental part
p. 6122 - 6126
(2011/12/01)
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- One-pot formation of piperidine- and pyrrolidine-substituted pyridinium salts via addition of 5-alkylaminopenta-2,4-dienals to N-acyliminium ions: Application to the synthesis of (±)-nicotine and analogs
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Addition of 5-alkylaminopenta-2,4-dienals onto N-acyliminium ions, generated in situ from α-hydroxycarbamates derived from pyrrolidine or piperidine, in the presence of zinc triflate, followed by dehydrative cyclization, allowed the formation of pyridinium salts substituted at their 3-position by a five- or six-membered nitrogen heterocycle. Subsequent N-dealkylation of the pyridinium moiety and deprotection of the secondary amine or reduction of the carbamate function led to (±)-nicotine and analogs.
- Peixoto, Sabrina,Nguyen, Tuan Minh,Crich, David,Delpech, Bernard,Marazano, Christian
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supporting information; experimental part
p. 4760 - 4763
(2010/12/25)
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- The photooxidative degradation of N-methylpyrrolidinone in the presence of Cs3PW12O40 and TiO2 colloid photocatalysts
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The mechanisms of the heterogeneous photocatalytic behavior of TiO2 and Cs3PW12O40 for the oxidative destruction of N-methylpyrrolidinone (NMP) in water are discussed. Both photocatalysts generate H-methylsuccinimide (NMS) and succinimide as the main intermediates from oxidation at the α-carbon and methyl positions. 2-Pyrrolidmone (2P) and 5-hydroxy-N-methylpyrrolidinone (5-HNMP) have also been identified as primary intermediates These intermediates are all broken down under further photooxidation. However, differences in product distribution indicate the possibility of several mechanistic pathways. Hydroxyl radical-like attack predominates for TiO2- photocatalyzed degradation, whereas the polyoxotungstate appears to oxidatrvely destroy NMP by both OH radical attack and direct oxidation For TiO2, the relative quantum yields for NMP oxidation (0.5 g L-1 TiO2, pH 3. 254 nm, 7 × 10-6 ein sec-1) increase from 3PW12O40 under the same conditions, the apparent quantum yield is nearly invariant (0.005-0.009) over the concentration range 10- 1000 ppm.
- Friesen, Duane A.,Headley, John V.,Langford, Cooper H.
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p. 3193 - 3198
(2007/10/03)
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- Ruthenium Tetroxide Oxidation of N-Alkyllactams
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Ruthenium tetroxide (RuO4) oxidation of N-alkyllactams proceeded regioselectively depending on the size of lactam ring, except for the seven-membered ring.Four- and eight-membered N-methyl- and N-ethyllactams were oxidized at the exocyclic α-carbon adjacent to nitrogen to produce the N-acyllactams and NH-lactams, while five- and six-membered lactams underwent endocyclic oxidation to yield the cyclic imides.Oxidation of seven-membered lactams yielded a mixture of products arising from both exocyclic and endocyclic oxidations.These regioselectivities were confirmed in the oxidation of substrates having a tertiary carbon at the oxidation position.Keywords---oxidation; ruthenium tetroxide oxidation; regioselective oxidation; hydroxylation; imide synthesis; N-alkyllactam; N-acyllactams; imide; ruthenium tetroxide; two-phase method
- Yoshifuji, Shigeyuki,Arakawa, Yukimi,Nitta, Yoshihiro
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p. 357 - 363
(2007/10/02)
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