1,3-Dipolar cycloaddition of nitrones: synthesis of multisubstituted, diverse range of heterocyclic compounds

被引:49
作者
Thakur, Seema [1 ]
Das, Arunima [1 ]
Das, Tapas [1 ]
机构
[1] NIT Jamshedpur, Dept Chem, Jamshedpur 831014, Bihar, India
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; BETA-LACTAM SYNTHESIS; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; UNPRECEDENTED SKELETON; BIOLOGICAL EVALUATION; AZAOXYALLYL CATIONS; KINETIC RESOLUTION; KINUGASA REACTION; CASCADE REACTIONS;
D O I
10.1039/d1nj02023d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cycloadditions are known to be one of the most abundant, versatile and valuable classes of chemical reactions. Among various efficient chemical processes, cycloaddition is an important route owing to its stereospecificity, ability to generate complex molecules and atom economy. Nitrone is one of the widely used dipoles in the 1,3-dipolar cycloaddition reaction, as it is stable and does not always require in situ generation. The 1,3-dipolar cycloaddition of nitrones with various dipolarophiles generates several heterocyclic rings having different sizes. These heterocycles have enormous applications in natural products, biologically active molecules and pharmaceuticals. This review is focused on nitrones that undergo cycloaddition with different substrates to generate various heterocyclic rings.
引用
收藏
页码:11420 / 11456
页数:37
相关论文
共 197 条
[151]  
Tabolin A. A., 2017, SYNTHESIS-STUTTGART, P3255
[152]   Origins of the β-lactam rings in natural products [J].
Tahlan, Kapil ;
Jensen, Susan E. .
JOURNAL OF ANTIBIOTICS, 2013, 66 (07) :401-410
[153]   Pyridovericin and pyridomacrolidin:: Novel metabolites from entomopathogenic fungi, Beauveria bassiana [J].
Takahashi, S ;
Kakinuma, N ;
Uchida, K ;
Hashimoto, R ;
Yanagisawa, T ;
Nakagawa, A .
JOURNAL OF ANTIBIOTICS, 1998, 51 (06) :596-598
[154]   Core-Structure-Motivated Design of a Phosphine-Catalyzed [3+2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles [J].
Tan, Bin ;
Candeias, Nuno R. ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (13) :4672-4675
[155]   A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides [J].
Teterina, Polina S. ;
Efremova, Mariia M. ;
Sirotkina, Ekaterina V. ;
Novikov, Alexander S. ;
Khoroshilova, Olesya V. ;
Molchanov, Alexander P. .
TETRAHEDRON LETTERS, 2019, 60 (39)
[156]   Cytotoxic Steroidal Alkaloids from Kibatalia laurifolia [J].
Thi Dao Phi ;
Van Cuong Pham ;
Huong Doan Thi Mai ;
Litaudon, Marc ;
Gueritte, Francoise ;
Van Hung Nguyen ;
Van Minh Chau .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (05) :1236-1240
[157]   A 19F NMR Label to Substitute Polar Amino Acids in Peptides: A CF3-Substituted Analogue of Serine and Threonine [J].
Tkachenko, Anton N. ;
Mykhailiuk, Pavel K. ;
Afonin, Sergii ;
Radchenko, Dmytro S. ;
Kubyshkin, Vladimir S. ;
Ulrich, Anne S. ;
Komarov, Igor V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1486-1489
[158]   Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines [J].
Tong, Mengchao ;
Zhang, Yong ;
Qin, Cong ;
Fu, Yiwei ;
Liu, Yonghai ;
Li, Hao ;
Wang, Wei .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20) :2945-2949
[159]  
Torssell K.B. G., 1998, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis
[160]   Pyrinodemin A, a cytotoxic pyridine alkaloid with an isoxazolidine moiety from sponge Amphimedon sp. [J].
Tsuda, M ;
Hirano, K ;
Kubota, T ;
Kobayashi, J .
TETRAHEDRON LETTERS, 1999, 40 (26) :4819-4820