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

来源：

NEW JOURNAL OF CHEMISTRY | 2021年 / 45卷 / 26期

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

页码：11420 / 11456

页数：37

共 197 条

[1] The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions.: Application in the total synthesis of the β-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid [J].

Aggarwal, VK ;

Roseblade, S ;

Alexander, R .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (04) :684-691

[2] Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition:: a concise asymmetric total synthesis of (-)-rosmarinecine [J].

Akai, S ;

Tanimoto, K ;

Kanao, Y ;

Omura, S ;

Kita, Y .

CHEMICAL COMMUNICATIONS, 2005, (18) :2369-2371

[3]

ALBEROLA A, 1982, SYNTHESIS-STUTTGART, P1067

[4] β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492

[5] REGIOSPECIFIC METAL-CATALYZED RING EXPANSION OF AZIRIDINES TO BETA-LACTAMS [J].

ALPER, H ;

URSO, F ;

SMITH, DJH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6737-6738

[6] Dankasterone, a new class of cytotoxic steroid produced by a Gymnascella species from a marine sponge [J].

Amagata, T ;

Doi, M ;

Tohgo, M ;

Minoura, K ;

Numata, A .

CHEMICAL COMMUNICATIONS, 1999, (14) :1321-1322

[7] Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2H-Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles [J].

Angyal, Aniko ;

Demjen, Andras ;

Wolfling, Janos ;

Puskas, Laszlo G. ;

Kanizsai, Ivan .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05) :3587-3595

[8] Application of 1,3-Dipolar Reactions between Azomethine Ylides and Alkenes to the Synthesis of Catalysts and Biologically Active Compounds [J].

Arrastia, Iosune ;

Arrieta, Ana ;

Cossio, Fernando P. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (43) :5889-5904

[9] Monamphilectine A, a Potent Antimalarial β-Lactam from Marine Sponge Hymeniacidon sp: Isolation, Structure, Semisynthesis, and Bioactivity [J].

Aviles, Edward ;

Rodriguez, Abimael D. .

ORGANIC LETTERS, 2010, 12 (22) :5290-5293

[10] The Rich Chemistry Resulting from the 1,3-Dipolar Cycloaddition Reactions of Enamines and Azides [J].

Bakulev, Vasiliy A. ;

Beryozkina, Tetyana ;

Thomas, Joice ;

Dehaen, Wim .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (03) :262-294

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