Formation of isoxazoles using cerium ammonium nitrate (CAN):: A one-pot synthesis of glycomimetics

被引：22

作者：

Beha, Sara ^{[1
]}

Giguere, Denis ^{[1
]}

Patnam, Ramesh ^{[1
]}

Roy, Rene ^{[1
]}

机构：

[1] Univ Quebec, Dept Chem, Montreal, PQ H3C 3P8, Canada

来源：

SYNLETT | 2006年 / 11期

关键词：

carbohydrates; cycloadditions; heterocycles; isoxazoles; CAN(IV);

D O I：

10.1055/s-2006-947330

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloaddition reactions of carbohydrate dipolarophiles with cerium(IV) ammonium nitrate CAN(IV) in acetone, acetophenone, or pinacolone yielded the corresponding 3,5-disubstituted isoxazoles, stable pharmacophores for glycomimetic syntheses.

引用

页码：1739 / 1743

页数：5

共 68 条

[51]

Padwa A., 1984, 1 3 DIPOLAR CYCLOADD

[52] Isoxazole-based derivatives from Baylis-Hillman chemistry: Assessment of preliminary hypolipidemic activity [J].

Patra, A ;

Batra, S ;

Bhaduri, AP ;

Khanna, A ;

Chander, R ;

Dikshit, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (10) :2269-2276

[53]

Roussel P, 2003, ADV EXP MED BIOL, V535, P17

[54]

Roy R, 2000, CHEM-EUR J, V6, P1757, DOI 10.1002/(SICI)1521-3765(20000515)6:10<1757::AID-CHEM1757>3.0.CO

[55]

2-5

[56] Transition metal catalyzed neoglycoconjugate syntheses [J].

Roy, R ;

Das, SK ;

Dominique, R ;

Trono, MC ;

Hernández-Mateo, F ;

Santoyo-González, F .

PURE AND APPLIED CHEMISTRY, 1999, 71 (04) :565-571

[57]

Roy R., 2005, ACS SYM SER, V896, P137, DOI DOI 10.1021/BK-2005-0896.CH008

[58]

ROY R, 2005, GLYCOMIMETICS MODERN, P137

[59]

SATO S, 2004, GLYCOCONJUGATE J, V19, P441

[60] Structure and function of Escherichia coli type 1 pili:: New insight into the pathogenesis of urinary tract infections [J].

Schilling, JD ;

Mulvey, MA ;

Hultgren, SJ .

JOURNAL OF INFECTIOUS DISEASES, 2001, 183 :S36-S40

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