Tin(II) Compounds as Catalysts for the Kabachnik-Fields Reaction under Solvent-Free Conditions: Facile Synthesis of α-Aminophosphonates

被引：45

作者：

Gallardo-Macias, Ricardo ^{[1
]}

Nakayama, Kensaku ^{[1
]}

机构：

[1] Calif State Univ Long Beach, Dept Chem & Biochem, Long Beach, CA 90840 USA

来源：

SYNTHESIS-STUTTGART | 2010年 / 01期

关键词：

alpha-aminophosphonates; catalysis; imines; Lewis acids; solvent-free; ONE-POT SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; AMINO PHOSPHONATES; 3-COMPONENT SYNTHESIS; ALDEHYDES; ACID;

D O I：

10.1055/s-0029-1217091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a catalytic amount of tin(II) salts, the three-component Kabachnik-Fields reaction involving aldehydes, amines, and diethyl phosphite proceeded smoothly to afford the corresponding alpha-aminophosphonates in good to high yields. These reactions were carried out under solvent-free conditions.

引用

页码：57 / 62

页数：6

共 36 条

[1] In-vitro activity of fosfomycin against vancomycin-resistant enterococci [J].

Allerberger, F ;

Klare, I .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1999, 43 (02) :211-217

[2]

Alonso E, 2000, SYNLETT, P698

[3] β,γ-Unsaturated α-aminophosphonates:: synthesis and reactivity [J].

Atmani, A ;

Combret, JC ;

Malhiac, C ;

Mulengi, JK .

TETRAHEDRON LETTERS, 2000, 41 (32) :6045-6048

[4] Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2003, 59 (28) :5329-5332

[5] An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate [J].

Bhagat, Srikant ;

Chakraborti, Asit K. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1263-1270

[6] Three component coupling catalyzed by TaCl5-SiO2:: synthesis of α-amino phosphonates [J].

Chandrasekhar, S ;

Prakash, SJ ;

Jagadeshwar, V ;

Narsihmulu, C .

TETRAHEDRON LETTERS, 2001, 42 (32) :5561-5563

[7]

CHERKASOV RA, 1998, RUSS CHEM REV, V67, P857, DOI [DOI 10.1070/RC1998V067N10ABEH000421, 10.1070/RC1998v067n10ABEH000421]

[8] Asymmetric synthesis of alpha-aminophosphonates via diastereoselective addition of phosphite to chiral imine derivatives [J].

Chung, SK ;

Kang, DH .

TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :21-24

[9] Metal triflate-catalyzed one-pot synthesis of α-aminophosphonates from carbonyl compounds in the absence of solvent [J].

Firouzabadi, H ;

Iranpoor, N ;

Sobhani, S .

SYNTHESIS-STUTTGART, 2004, (16) :2692-2696

[10]

Galkina I V., 1998, Russ. J. Gen. Chem, V68, P1402

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