Ionic-liquid-supported synthesis of amines and derivatives

被引：28

作者：

Debdab, Mansour ^{[1
]}

Mongin, Florence ^{[1
]}

Bazureau, Jean Pierre ^{[1
]}

机构：

[1] Univ Rennes 1, CNRS, UMR 6510, F-35043 Rennes, France

来源：

SYNTHESIS-STUTTGART | 2006年 / 23卷 / 23期

关键词：

ionic liquids; amines; glycine derivatives; esters; Ugi reaction;

D O I：

10.1055/s-2006-950309

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amine precursors such as glycines protected at nitrogen with a Boc or formyl group were grafted by esterification on the hydroxylated arms of 1-(2-hydroxyethyl)-3-methylimidazolium hexafluorophosphates or tetrafluoroborates. The cleavage of the Boc group was then realized at room temperature by successively treating acetonitrile solutions of the thus formed glycinates with methanol and acetyl chloride (two equivalents each). Interestingly, the resulting glycinate hydrochlorides were converted into the corresponding amines during the removal of the solvent. Ugi reaction of one of these ionic-liquid-grafted amines with phthalaldehydic acid and tert-butyl isocyanide, followed by cleavage, furnished a phthalimidine.

引用

页码：4046 / 4052

页数：7

共 31 条

[1] Thermal solid state synthesis of coordination complexes from hydrogen bonded precursors [J].

Adams, CJ ;

Crawford, PC ;

Orpen, AG ;

Podesta, TJ ;

Salt, B .

CHEMICAL COMMUNICATIONS, 2005, (19) :2457-2458

[2] Synthesis and preliminary use of novel acrylic ester-derived task-specific ionic liquids [J].

Anjaiah, S ;

Chandrasekhar, S ;

Grée, R .

TETRAHEDRON LETTERS, 2004, 45 (03) :569-571

[3] Palladium catalysed tandem cyclisation-anion capture.: Part 7:: Synthesis of derivatives of α-amino esters, nitrogen heterocycles and β-aryl/heteroaryl ethylamines via in situ generated vinylstannanes [J].

Casaschi, A ;

Grigg, R ;

Sansano, JM .

TETRAHEDRON, 2001, 57 (03) :607-615

[4] Development of a novel ionic support and its application in the ionic liquid phase assisted synthesis of a potent antithrombotic [J].

de Kort, M ;

Tuin, AW ;

Kuiper, S ;

Overkleeft, HS ;

van der Marel, GA ;

Buijsman, RC .

TETRAHEDRON LETTERS, 2004, 45 (10) :2171-2175

[5]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

[6]

2-U

[7] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

[8] Synthesis of diverse tetrahydro-β-carboline-3-carboxamides and -2,3-bis-lactams on a versatile 4-hydroxythiophenol-linked solid support [J].

Fantauzzi, PP ;

Yager, KM .

TETRAHEDRON LETTERS, 1998, 39 (11) :1291-1294

[9] Synthesis of α-isocyano-α-alkyl(aryl)acetamides and their use in the multicomponent synthesis of 5-aminooxazole, pyrrolo[3,4-b]pyridin-5-one and 4,5,6,7-tetrahydrofuro[2,3-c]pyridine [J].

Fayol, A ;

Housseman, C ;

Sun, XW ;

Janvier, P ;

Bienaymé, H ;

Zhu, JP .

SYNTHESIS-STUTTGART, 2005, (01) :161-165

[10] Ecofriendly fast synthesis of hydrophilic poly(ethyleneglycol)-ionic liquid matrices for liquid-phase organic synthesis [J].

Fraga-Dubreuil, J ;

Famelart, MH ;

Bazureau, JP .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (04) :374-378

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