scholarly journals New Bicyclic Azalide Macrolides Obtained by Tandem Palladium Catalyzed Allylic Alkylation/Conjugated Addition Reaction

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 432
Author(s):  
Sulejman Alihodžić ◽  
Hana Čipčić Paljetak ◽  
Ana Čikoš ◽  
Ivaylo Jivkov Elenkov
Keyword(s):  
Antibacterial Activity ◽  
Nmr Spectroscopy ◽  
Chemical Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Allylic Alkylation ◽  
Antibiotic Drug ◽  
Palladium Catalyzed

Unprecedented tandem allylic alkylation/intermolecular Michael addition was used in the preparation of novel bicyclic azalides. NMR spectroscopy was used not only to unambiguously determine and characterize the structures of these unexpected products of chemical reaction but also to investigate the effect the rigid bicyclic modification has on the conformation of the whole molecule. Thus, some of the macrolides prepared showed antibacterial activity in the range of well-known antibiotic drug azithromycin.

scholarly journals NMR spectroscopy study on N,N′-bismaleimide-4,4′-diphenylmethane and barbituric acid synthesis reaction mechanism in N,N′-dimethylformamide solvent

RSC Advances ◽  
2017 ◽  
Vol 7 (2) ◽  
pp. 651-661
Author(s):  
Yuan-Chun Wen ◽  
Yuan-Chun Sue ◽  
Shan-Yuan Yang ◽  
Jing-Pin Pan ◽  
Tsung-Hsiung Wang ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Nmr Spectroscopy ◽  
Michael Addition ◽  
Barbituric Acid ◽  
Addition Reaction ◽  
Acid Synthesis ◽  
Synthesis Reaction ◽  
Spectroscopy Study ◽  
Michael Addition Reaction

1H signal assignments of C1N0E, C1N0K, C2N0A, C2N0S model products of Michael addition reaction in STOBA-like synthesis.

The six-membered annulation reaction involving sequential palladium-catalyzed allylic alkylation and Michael addition: scope and limitations

Tetrahedron ◽  
2003 ◽  
Vol 59 (12) ◽  
pp. 2093-2099 ◽  
Author(s):  
Céline Jousse-Karinthi ◽  
Fatima Zouhiri ◽  
Jacqueline Mahuteau ◽  
Didier Desmaële
Keyword(s):  
Michael Addition ◽  
Allylic Alkylation ◽  
Palladium Catalyzed

The Six-Membered Annulation Reaction Involving Sequential Palladium-Catalyzed Allylic Alkylation and Michael Addition: Scope and Limitations.

ChemInform ◽  
2003 ◽  
Vol 34 (28) ◽  
Author(s):  
Celine Jousse-Karinthi ◽  
Fatima Zouhiri ◽  
Jacqueline Mahuteau ◽  
Didier Desmaele
Keyword(s):  
Michael Addition ◽  
Allylic Alkylation ◽  
Palladium Catalyzed

Palladium-catalyzed Synthesis of Novel O-Heterocycles by Domino Suzuki Coupling-Michael Addition Reaction

2015 ◽  
Vol 53 (3) ◽  
pp. 919-923 ◽  
Author(s):  
Qihua Zhu ◽  
Feng Nie ◽  
Jingjie Feng ◽  
Yuyan Li ◽  
Xuyan Wang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Suzuki Coupling ◽  
Michael Addition Reaction ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Synthesis of Novel O-Heterocycles by Domino Suzuki Coupling-Michael Addition Reaction

ChemInform ◽  
2016 ◽  
Vol 47 (35) ◽  
Author(s):  
Qihua Zhu ◽  
Feng Nie ◽  
Jingjie Feng ◽  
Yuyan Li ◽  
Xuyan Wang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Suzuki Coupling ◽  
Michael Addition Reaction ◽  
Palladium Catalyzed

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

2020 ◽  
Author(s):  
Kiron Kumar Ghosh ◽  
Alexander Uttry ◽  
Francesca Ghiringhelli ◽  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Michael Addition ◽  
Kinetic Studies ◽  
Wide Range ◽  
Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

2019 ◽  
Author(s):  
Nobutaka Fujieda ◽  
Miho Yuasa ◽  
Yosuke Nishikawa ◽  
Genji Kurisu ◽  
Shinobu Itoh ◽  
...  
Keyword(s):  
Michael Addition ◽  
In Silico ◽  
Addition Reaction ◽  
Single Point ◽  
Point Mutations ◽  
Unsaturated Ketone ◽  
Michael Addition Reaction ◽  
Beta Barrel ◽  
Cupin Superfamily ◽  
Single Point Mutations

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

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