Highly efficient ring opening reactions of epoxides with deactivated aromatic amines catalyzed by heteropoly acids in water

被引：81

作者：

Azizi, Najmedin

Saidi, Mohammad R.

机构：

[1] Sharif Univ Technol, Dept Chem, Tehran, Iran

[2] Chem & Chem Engn Res Ctr Iran, Tehran, Iran

来源：

TETRAHEDRON | 2007年 / 63卷 / 04期

关键词：

amino alcohol; aromatic amine; epoxide; heteropoly acid; atom economy; water chemistry;

D O I：

10.1016/j.tet.2006.11.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heteropoly acid was found to be an effective and efficient catalyst for the ring opening reaction of epoxides with various aromatic amines to produce the corresponding (3-amino alcohols in moderate to excellent yields in water. This method provides a new and efficient protocol in terms of mild reaction conditions, clean reaction profiles, small quantity of catalyst, and simple work-up procedure. (c) 2006 Published by Elsevier Ltd.

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页码：888 / 891

页数：4

相关论文

共 39 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2] One-pot synthesis of dithiocarbamates accelerated in water [J].

Azizi, N ;

Aryanasab, F ;

Torkiyan, L ;

Ziyaei, A ;

Saidi, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3634-3635

[3] Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids [J].

Azizi, N ;

Torkiyan, L ;

Saidi, MR .

ORGANIC LETTERS, 2006, 8 (10) :2079-2082

[4] LiClO4•3H2O promoted highly regioselective ring-opening of epoxides with thiols under neutral conditions [J].

Azizi, N ;

Saidi, MR .

CATALYSIS COMMUNICATIONS, 2006, 7 (04) :224-227

[5] Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispersed in silica gel under neutral condition [J].

Azizi, N ;

Yousefi, R ;

Saidi, MR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (05) :817-820

[6] Highly chemoselective addition of amines to epoxides in water [J].

Azizi, N ;

Saidi, MR .

ORGANIC LETTERS, 2005, 7 (17) :3649-3651

[7] A mild and highly efficient protocol for the one-pot synthesis of primary α-amino phosphonates under solvent-free conditions [J].

Azizi, N ;

Rajabi, F ;

Saidi, MR .

TETRAHEDRON LETTERS, 2004, 45 (50) :9233-9236

[8] Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions [J].

Azizi, N ;

Saidi, MR .

ORGANOMETALLICS, 2004, 23 (06) :1457-1458

[9] LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2004, 60 (02) :383-387

[10] DISODIUM (R,R)-5-[2-[[2-(3-CHLOROPHENYL)-2-HYDROXYETHYL]AMINO]PROPYL]-1,3-BENZODIOXOLE-2,2-DICARBOXYLATE (CL 316,243) - A POTENT BETA-ADRENERGIC AGONIST VIRTUALLY SPECIFIC FOR BETA-3 RECEPTORS - A PROMISING ANTIDIABETIC AND ANTIOBESITY AGENT [J].

BLOOM, JD ;

DUTIA, MD ;

JOHNSON, BD ;

WISSNER, A ;

BURNS, MG ;

LARGIS, EE ;

DOLAN, JA ;

CLAUS, TH .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (16) :3081-3084

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