共 21 条
- [21] Synthesis of spiro[piperidine-4,3 ′-pyrrolo[3,4- c ]quinolines via 1,3-dipolar cycloaddition of azomethine ylides and 3-Nitro-2(1 H )-quinolonesTETRAHEDRON LETTERS, 2024, 139Molnar, MarkGati, TamasBenyei, AttilaNyerges, Miklos
Five-Membered Nitrogen Heterocycles Synthesis through 1,3-Dipolar Cycloaddition of Non-Stabilized Azomethine Ylides with 2-Pyridone Heteroaromatic Systems as Dipolarophiles
被引：10
|作者：
Ben Salah, Sami
[1
,2
]
Sanselme, Morgane
[1
,3
]
Champavier, Yves
[4
]
Othman, Mohamed
[1
,2
]
Daich, Adam
[1
,2
]
Chataigner, Isabelle
[5
,6
]
Lawson, Ata Martin
[1
,2
]
机构：
[1] Normandie Univ, Rouen, France
[2] UNILEHAVRE, CNRS, URCOM, EA 3212,INC3 M,FR 3038, F-76600 Le Havre, France
[3] UNIROUEN, Lab SMS EA 3233, 1 Rue Tesniere, F-76821 Mont St Aignan, France
[4] Ctr Biol Rech & Sante, UMS2015 CNRS, US042 INSERM, PEIRENE EA 7500 BISCEm, 2 Rue Dr Marcland, F-87025 Limoges, France
[5] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA Lab, F-76000 Rouen, France
[6] Sorbonne Univ, CNRS, LCT UMR 7616, F-75005 Paris, France
关键词：
Azomethine ylide;
1;
3-Cycloaddition;
Fused-pyridones;
2-Pyridones;
Pyrrolidine ring construction;
DIELS-ALDER CYCLOADDITIONS;
AMARYLLIDACEAE ALKALOIDS;
ISOQUINOLINE DERIVATIVES;
FACILE DEAROMATIZATION;
DOMINO PROCESS;
N-ALKYLATION;
WHOLE PLANTS;
2(1H)-PYRIDONES;
PYRROLIDINES;
ALKENES;
D O I：
10.1002/ejoc.202001404
中图分类号：
O62 [有机化学];
学科分类号：
070303 ;
081704 ;
摘要：
We report an efficient 1,3-dipolar cycloaddition involving non-stabilized electron-rich azomethine ylides and diversely substituted 2-pyridones bearing two potential C=C dipolarophilic sites. The 1,3-dipoles were prepared in situ under TFA catalysis and cycloadditions were studied according to the nature of the pyridones and position of the various substituents. These reactions occur under mild conditions, and lead to the expected cycloadducts in good yields and full control of the regioselectivity. Furthermore, mono- or biscycloadditions were performed, leading to the formation of polycyclic scaffolds bearing biologically relevant pyrrolidine rings, prevalent in natural products. The diastereoselectivity of the second cycloaddition was fully controlled by the first addition, leading to heterocycles with a trans relative stereochemistry of the two generated rings in the final tricyclo-adduct.
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页码：102 / 116
页数：15
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