An efficient synthesis of β,γ,γ-trisubstituted-α-diethoxyphosphoryl-γ-lactams: a convenient approach to α-methylene-γ-lactams

被引:11
作者
Deredas, Dariusz [1 ]
Albrecht, Lukasz [1 ]
Krawczyk, Henryk [1 ]
机构
[1] Tech Univ Politech, Inst Organ Chem, PL-90924 Lodz, Poland
关键词
Michael addition; Olefination; alpha-Diethoxyphosphoryl-gamma-lactams; alpha-Methylene-gamma-lactams; 1,1,3,3-Tetramethylguanidine; BAYLIS-HILLMAN ADDUCTS; CYTOTOXIC EVALUATION; LACTONES; ACID;
D O I
10.1016/j.tetlet.2013.03.130
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and efficient method for the preparation of beta,gamma,gamma-trisubstituted-alpha-phosphono-gamma-lactams is presented for the first time. This approach is based on the Michael addition of diethyl acetamidomalonate to methyl (E)-3-aryl-2-(diethoxyphosphoryl)acrylates. Application of the phosphono-lactams obtained for the preparation of alpha-methylene-gamma-lactams is also reported. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3088 / 3090
页数:3
相关论文
共 24 条
[1]   Synthesis and cytotoxic activity of γ-aryl substituted α-alkylidene-γ-lactones and α-alkylidene-γ-lactams [J].
Albrecht, Anna ;
Koszuk, Jacek F. ;
Modranka, Jakub ;
Rozalski, Marek ;
Krajewska, Urszula ;
Janecka, Anna ;
Studzian, Kazimierz ;
Janecki, Tomasz .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (09) :4872-4882
[2]   Recent Advances in the Synthesis of α-Alkylidene-Substituted δ-Lactones, γ-Lactams and δ-Lactams [J].
Albrecht, Anna ;
Albrecht, Lukasz ;
Janecki, Tomasz .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) :2747-2766
[3]   A convenient synthesis and cytotoxic evaluation of β-aryl-α-methylidene-γ-lactones and β-aryl-α-methylidene-γ-lactams [J].
Albrecht, Anna ;
Albrecht, Lukasz ;
Rozalski, Marek ;
Krajewska, Urszula ;
Janecka, Anna ;
Studzian, Kazimierz ;
Janecki, Tomasz .
NEW JOURNAL OF CHEMISTRY, 2010, 34 (04) :750-761
[4]   SYNTHESIS OF POTENTIAL CYTOTOXIC ALPHA-METHYLENE GAMMA-LACTAMS [J].
BELAUD, C ;
ROUSSAKIS, C ;
LETOURNEUX, Y ;
ELALAMI, N ;
VILLIERAS, J .
SYNTHETIC COMMUNICATIONS, 1985, 15 (14) :1233-1243
[5]   2-Diethoxyphosphoryl-4-nitroalkanoates -: Versatile intermediates in the synthesis of α-alkylidene-γ-lactones and lactams [J].
Blaszczyk, E ;
Krawczyk, H ;
Janecki, T .
SYNLETT, 2004, (15) :2685-2688
[6]  
Cardellina J.H., 1979, TETRAHEDRON LETT, V22, P2007
[7]   Synthesis of (2S,3S)-[3-2H1]-4-methyleneglutamic acid and (2S,3R)-[2,3-2H2]-4-methyleneglutamic acid [J].
Dieterich, P ;
Young, DW .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (08) :1492-1496
[8]   Imine allylation using 2-alkoxycarbonyl allylboronates as an expedient three-component reaction to polysubstituted α-exo-methylene-γ-lactams [J].
Elford, Tim G. ;
Hall, Dennis G. .
TETRAHEDRON LETTERS, 2008, 49 (49) :6995-6998
[9]   Diversity-Oriented Synthesis and Preliminary Biological Screening of Highly Substituted Five-Membered Lactones and Lactams Originating From an Allyboration of Aldehydes and Imines [J].
Elford, Tim G. ;
Ulaczyk-Lesanko, Agnieszka ;
De Pascale, Gianfranco ;
Wright, Gerard D. ;
Hall, Dennis G. .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (01) :155-168
[10]  
EZQUERRA J, 1994, TETRAHEDRON-ASYMMETR, V5, P921