Azomethine Ylides-Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

被引：20

作者：

Panda, Siva S. ^{[1
]}

Aziz, Marian N. ^{[2
]}

Stawinski, Jacek ^{[3
,4
]}

Girgis, Adel S. ^{[2
]}

机构：

[1] Augusta Univ, Dept Chem & Phys, Augusta, GA 30912 USA

[2] Natl Res Ctr, Dept Pesticide Chem, Giza 12622, Egypt

[3] Polish Acad Sci, Inst Bioorgan Chem, Noskowskiego 12-14, PL-61704 Poznan, Poland

[4] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

来源：

MOLECULES | 2023年 / 28卷 / 02期

关键词：

cycloaddition; azomethine ylide; pyrrolidine; spiro-compound; 1,3-DIPOLAR CYCLOADDITION REACTIONS; BAYLIS-HILLMAN ADDUCTS; ONE-POT SYNTHESIS; CHOLINESTERASE INHIBITORY-ACTIVITY; ANTI-ONCOLOGICAL ALKALOIDS; MEDIATED 3+2 CYCLOADDITION; SPIRO-PYRIDO-PYRROLIZINES; ATOM ECONOMIC SYNTHESIS; REGIOSELECTIVE-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.3390/molecules28020668

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Azomethine ylides are nitrogen-based three-atom components commonly used in [3+2]-cycloaddition reactions with various unsaturated 2 pi-electron components. These reactions are highly regio- and stereoselective and have attracted the attention of organic chemists with respect to the construction of diverse heterocycles potentially bearing four new contiguous stereogenic centers. This review article complies the most important [3+2]-cycloaddition reactions of azomethine ylides with various olefinic, unsaturated 2 pi-electron components (acyclic, alicyclic, heterocyclic, and exocyclic ones) reported over the past two decades.

引用

页数：81

共 179 条

[1] Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].

Adrio, Javier ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2019, 55 (80) :11979-11991

[2] Synthesis of Spiro[indole-3,5′-isoxazoles] with Anticancer Activity via a Formal [4+1]-Spirocyclization of Nitroalkenes to Indoles [J].

Aksenov, Alexander V. ;

Aksenov, Dmitrii A. ;

Arutiunov, Nikolai A. ;

Aksenov, Nicolai A. ;

Aleksandrova, Elena V. ;

Zhao, Zhenze ;

Du, Liqin ;

Kornienko, Alexander ;

Rubin, Michael .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) :7123-7137

[3] Synthesis of novel dispiro-oxindoles via 1,3-dipolar cycloaddition reactions of azomethine ylides [J].

Al Mamari, Khalil ;

Ennajih, Hamid ;

Zouihri, Hafid ;

Bouhfid, Rachid ;

Ng, Seik Weng ;

Essassi, El Mokhtar .

TETRAHEDRON LETTERS, 2012, 53 (18) :2328-2331

[4] AChE inhibitor: A regio- and stereo-selective 1,3-dipolar cycloaddition for the synthesis of novel substituted 5,6-dimethoxy spiro[5.3′]-oxindole-spiro-[6.3"]-2,3-dihydro-1H-inden-1"-one-7-(substituted aryl)-tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole [J].

Ali, Mohamed Ashraf ;

Ismail, Rusli ;

Choon, Tan Soo ;

Kumar, Raju Suresh ;

Osman, Hasnah ;

Arumugam, Natarajan ;

Almansour, Abdulrahman I. ;

Elumalai, Karthikeyan ;

Singh, Abhimanyu .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (01) :508-511

[5] Substituted spiro [2.3′] oxindolespiro [3.2"]-5,6-dimethoxy-indane-1"-one-pyrrolidine analogue as inhibitors of acetylcholinesterase [J].

Ali, Mohamed Ashraf ;

Ismail, Rusli ;

Choon, Tan Soo ;

Yoon, Yeong Keng ;

Wei, Ang Chee ;

Pandian, Suresh ;

Kumar, Raju Suresh ;

Osman, Hasnah ;

Manogaran, Elumalai .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) :7064-7066

[6] An experimental and theoretical investigation of the regio- and stereoselectivity of the polar [3+2] cycloaddition of azomethine ylides to nitrostyrenes [J].

Alimohammadi, Kamal ;

Sarrafi, Yaghoub ;

Tajbakhsh, Mahmood ;

Yeganegi, Saeed ;

Hamzehloueian, Mahshid .

TETRAHEDRON, 2011, 67 (08) :1589-1597

[7] Design, synthesis and cholinesterase inhibitory activity of novel spiropyrrolidine tethered imidazole heterocyclic hybrids [J].

Almansour, Abdulrahman, I ;

Arumugam, Natarajan ;

Kumar, Raju Suresh ;

Kotresha, D. ;

Manohar, Thota Sai ;

Venketesh, S. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2020, 30 (02)

[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] A novel access to highly functionalised β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction [J].

Arumugam, N ;

Jayashankaran, J ;

Manian, RDRS ;

Raghunathan, R .

TETRAHEDRON, 2005, 61 (35) :8512-8516

[10] Anti-tubercular activity of novel class of spiropyrrolidine tethered indenoquinoxaline heterocyclic hybrids [J].

Arumugam, Natarajan ;

Almansour, Abdulrahman, I ;

Kumar, Raju Suresh ;

Alaqeel, Shatha Ibrahim ;

Krishna, Vagolu Siva ;

Sriram, Dharmarajan .

BIOORGANIC CHEMISTRY, 2020, 99

← 1 2 3 4 5 6 7 8 9 10 →