Efficient method for the synthesis of 1,2,3-triazole functionalized isoxazolidine derivatives by 1,3-dipolar cycloaddition of nitrones with terminal olefins

被引：1

作者：

Rao, P. Sambasiva ^{[1
]}

Ashalu, K. Chinna ^{[1
]}

Dev, G. Jitender ^{[1
]}

Ravi Kumar, N. ^{[1
]}

Srinivas, P. V. S. S. ^{[1
]}

Thomas, B. V. ^{[1
]}

Narsaiah, B. ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Fluoroorgan Div, Tarnaka 500007, Hyderabad, India

来源：

SYNTHETIC COMMUNICATIONS | 2017年 / 47卷 / 05期

关键词：

1,3-Dipolar cycloaddition; isoxazolidine; nitrones; olefins; 1,2,3-triazole; BIOLOGICAL EVALUATION; CYCLIC NITRONES; NUCLEOSIDES;

D O I：

10.1080/00397911.2016.1271133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Phenyl-1,2,3-triazole-4-carbaldehyde 1 was treated with different N-alkyl hydroxylamine hydrochlorides 2 using NaHCO3 to obtain 1,2,3-triazole substituted N-alkyl nitrones 3a-c. The nitrones 3a-c were further reacted with different substituted olefins and furnished 2-alkyl-3-(1-phenyl-1H-1,2,3-triazol-4-yl)-5-(substituted)isoxazolidine derivatives 4a-p in high yields via 1,3-dipolar cycloaddition reaction.

引用

页码：457 / 462

页数：6

共 33 条

[1]

ALI SA, 1988, TETRAHEDRON, V44, P5911

[2] STEREOSELECTIVE INTRAMOLECULAR NITRONE CYCLOADDITIONS TO CHIRAL ALLYL ETHERS [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L .

TETRAHEDRON, 1987, 43 (17) :4051-4056

[3] Stereoselective synthesis of 1,2,3-triazolyl-functionalized isoxazolidines, via two consecutive 1,3-dipolar cycloadditions, as precursors of unnatural amino acids [J].

Aouadi, Kaiss ;

Vidal, Sebastien ;

Msaddek, Moncef ;

Praly, Jean-Pierre .

TETRAHEDRON LETTERS, 2013, 54 (15) :1967-1971

[4] Diastereo- and enantioselective synthesis of N,O-nucleosides [J].

Chiacchio, U ;

Corsaro, A ;

Iannazzo, D ;

Piperno, A ;

Pistarà, V ;

Rescifina, A ;

Romeo, R ;

Sindona, G ;

Romeo, G .

TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2717-2723

[5] Homochiral α-D- and β-D-isoxazolidinylthymidines via 1,3-dipolar cycloaddition [J].

Chiacchio, U ;

Corsaro, A ;

Gumina, G ;

Rescifina, A ;

Iannazzo, D ;

Piperno, A ;

Romeo, G ;

Romeo, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9321-9327

[6]

De Clercq E, 2002, MED RES REV, V22, P531

[7] A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF ALLYLIC AND HOMOALLYLIC AMINES [J].

DESHONG, P ;

LEGINUS, JM ;

LANDER, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :574-576

[8] 1,3-Dipolar cycloaddition of stabilised and non-stabilised azomethine ylides derived from uracil polyoxin C (UPoC): access to nikkomycin analogues [J].

Dondas, HA ;

Fishwick, CWG ;

Grigg, R ;

Kilner, C .

TETRAHEDRON, 2004, 60 (15) :3473-3485

[9] Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides [J].

Giofre, Salvatore V. ;

Romeo, Roberto ;

Carnovale, Caterina ;

Mancuso, Raffaella ;

Cirmi, Santa ;

Navarra, Michele ;

Garozzo, Adriana ;

Chiacchio, Maria A. .

MOLECULES, 2015, 20 (04) :5260-5275

[10] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

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