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

被引:47
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
[71]   Recent Advances in Asymmetric Organocatalytic Construction of 3,3′-Spirocyclic Oxindoles [J].
Hong, Liang ;
Wang, Rui .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) :1023-1052
[72]   Recent advances in β-lactam synthesis [J].
Hosseyni, Seyedmorteza ;
Jarrahpour, Aliasghar .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (38) :6840-6852
[73]   Recent Developments in the Synthesis and Reactivity of Isoxazoles: Metal Catalysis and Beyond [J].
Hu, Feng ;
Szostak, Michal .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (12) :2583-2614
[74]   Asymmetric Rh(II)/Pd(0) Relay Catalysis: Synthesis of α-Quaternary Chiral β-Lactams through Enantioselective C-H Insertion/Diastereoselective Allylation of Diazoamides [J].
Huang, Liang-Zhu ;
Xuan, Zi ;
Jeon, Hyun Ji ;
Du, Zhen-Ting ;
Kim, Ju Hyun ;
Lee, Sang-gi .
ACS CATALYSIS, 2018, 8 (08) :7340-7345
[75]   Enantioselective Synthesis of Indole-Annulated Medium-Sized Rings [J].
Huang, Lin ;
Dai, Li-Xin ;
You, Shu-Li .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (18) :5793-5796
[76]   Stereoselective Synthesis of β-Lactam-triflones under Catalyst-Free Conditions [J].
Huang, Zhongyan ;
Wang, Chen ;
Tokunaga, Etsuko ;
Sumii, Yuji ;
Shibata, Norio .
ORGANIC LETTERS, 2015, 17 (22) :5610-5613
[77]   A Unique Approach to the Concise Synthesis of Highly Optically Active Spirooxazolines and the Discovery of a More Potent Oxindole-Type Phytoalexin Analogue [J].
Jiang, Xianxing ;
Cao, Yiming ;
Wang, Yiqing ;
Liu, Luping ;
Shen, Fangfang ;
Wang, Rui .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15328-15333
[78]   MAGNESIUM BROMIDE-PROMOTED E/Z-ISOMERIZATION OF CARBONYL-CONJUGATED NITRONES AND HIGHLY STEREOSELECTIVE AND REGIOSELECTIVE CYCLOADDITIONS TO ALLYLIC ALCOHOL DIPOLAROPHILES [J].
KANEMASA, S ;
TSURUOKA, T .
CHEMISTRY LETTERS, 1995, (01) :49-50
[79]   Highly endo- and enantioselective asymmetric nitrone cycloadditions catalyzed by the aqua complex of 4,6-dibenzofurandiyl-2,2′-bis (4-phenyl-oxazoline)-nickel(II) perchlorate.: Transition structure based on dramatic effect of MS 4A on selectivities [J].
Kanemasa, S ;
Oderaotoshi, Y ;
Tanaka, J ;
Wada, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) :12355-12356
[80]   Asymmetric 1,3-dipolar cycloaddition reaction of nitrones and acrolein with a bis-titanium catalyst as chiral lewis acid [J].
Kano, T ;
Hashimoto, T ;
Maruoka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :11926-11927