Rearrangement of Pyran Derivatives Obtained from Vinyl Malononitriles and Aldehydes via Vinylogous Aldol Reaction: A Novel Facile Method for the Synthesis of Dienamides

被引:17
作者
Babu, Thelagathoti Hari [1 ]
Pawar, Sujeet [1 ]
Muralidharan, D. [1 ]
Perumal, Paramasivan T. [1 ]
机构
[1] Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India
关键词
vinyl malononitrile; vinylogous aldol reaction; pyran rearrangement; dienamides; CHONDROMYCES-SPECIES MYXOBACTERIA; RUTHENIUM AMIDO COMPLEXES; DIELS-ALDER REACTIONS; TRANSFER HYDROGENATION; EFFICIENT SYNTHESIS; MARINE SPONGE; ISOCYANATES; APICULARENS; CYCLIZATION; MACROLIDES;
D O I
10.1055/s-0030-1258522
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel one-pot approach to a variety dienamides from vinyl malononitriles and aldehydes via vinylogous aldol reaction was achieved by the electrolytic ring opening of the initially formed pyran derivatives under mild basic catalysis with good diastereoselectivity.
引用
收藏
页码:2125 / 2129
页数:5
相关论文
共 44 条
[1]  
Abarbri M, 1996, SYNTHESIS-STUTTGART, P82
[2]   A synthetic approach to natural dienamides of insecticidal interest [J].
Abarbri, M ;
Parrain, JL ;
Duchêne, A .
SYNTHETIC COMMUNICATIONS, 1998, 28 (02) :239-249
[3]   A Facile, One-Pot Synthesis of Functionalized Spiro-Oxindoles via Vinylogous Aldol Reaction of Vinyl Malononitriles with Isatin Derivatives in Aqueous Media [J].
Babu, Thelagathoti Hari ;
Karthik, K. ;
Perumal, Paramasivan T. .
SYNLETT, 2010, (07) :1128-1132
[4]   A novel method for the synthesis of functionalized spirocyclic oxindoles by one-pot tandem reaction of vinyl malononitriles with isatylidene malononitriles [J].
Babu, Thelagathoti Hari ;
Joseph, A. Abragam ;
Muralidharan, D. ;
Perumal, Paramasivan T. .
TETRAHEDRON LETTERS, 2010, 51 (06) :994-996
[5]   Asymmetric induction of the lodolactonization reaction of α-sulfurated γ-unsaturated amides [J].
Blot, V ;
Reboul, V ;
Metzner, P .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1196-1201
[6]   The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].
Casiraghi, G ;
Zanardi, F ;
Appendino, G ;
Rassu, G .
CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972
[7]   Efficient asymmetric transfer hydrogenation of activated olefins catalyzed by ruthenium amido complexes [J].
Chen, YC ;
Xue, D ;
Deng, JG ;
Cui, X ;
Zhu, J ;
Jiang, YZ .
TETRAHEDRON LETTERS, 2004, 45 (07) :1555-1558
[8]   Synthesis of aromatic (E)- or (Z)-α,β-unsaturated amides with total or very high selectivity from α,β-epoxyamides and samarium diiodide [J].
Concellón, JM ;
Bardales, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9492-9495
[9]   Nickel-Catalyzed Cycloadditive Couplings of Enynes and Isocyanates [J].
D'Souza, Brendan R. ;
Louie, Janis .
ORGANIC LETTERS, 2009, 11 (18) :4168-4171
[10]  
Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338