Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

被引:40
作者
Abbiati, Giorgio [1 ]
Arcadi, Antonio [2 ]
Marinelli, Fabio [2 ]
Rossi, Elisabetta [1 ]
机构
[1] Univ Milan, Dipartimento Sci Farmaceut, Sez Chim Gen & Organ A Marchesini, I-20133 Milan, Italy
[2] Univ Aquila, Dipartimento Sci Fis & Chim, I-67010 Laquila, Italy
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 06期
关键词
aminoalkynones; hydroxyalkynoates; sequential reactions; annulation; heterocycles; RHODIUM-CATALYZED ADDITION; HIGHLY SUBSTITUTED FURANS; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; POT 3-COMPONENT SYNTHESIS; ALPHA-AMINO ESTERS; EFFICIENT SYNTHESIS; ARYLBORONIC ACIDS; ARYL IODIDES; GAMMA-HYDROXY-ALPHA; BETA-ACETYLENIC ESTERS; ELECTROPHILIC CYCLIZATION;
D O I
10.1055/s-0033-1338594
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review examines sequential processes involving alpha,beta-ynones and alpha,beta-ynoates containing proximate nucleophiles as useful building blocks for the synthesis of heterocyclic derivatives through conjugate-addition-type, pericyclic and transition-metal-catalyzed transfer hydrogenation, hydroarylation, hydrovinylation, or hydroalkynylation reactions followed by heterocyclization.
引用
收藏
页码:687 / 721
页数:35
相关论文
共 224 条
[1]   Palladium-assisted multicomponent synthesis of 2-aryl-4-aminoquinolines and 2-aryl-4-amino[1,8]naphthyridines [J].
Abbiati, G ;
Arcadi, A ;
Canevari, V ;
Capezzuto, L ;
Rossi, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6454-6460
[2]   Intramolecular cyclization of δ-iminoacetylenes:: A new entry to pyrazino[1,2-a]indoles [J].
Abbiati, G ;
Arcadi, A ;
Bellinazzi, A ;
Beccalli, E ;
Rossi, E ;
Zanzola, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4088-4095
[3]   Novel intramolecular cyclization of N-alkynyl heterocycles containing proximate nucleophiles [J].
Abbiati, G ;
Arcadi, A ;
Beccalli, E ;
Rossi, E .
TETRAHEDRON LETTERS, 2003, 44 (28) :5331-5334
[4]  
Abbiati G, 2003, EUR J ORG CHEM, V2003, P1423
[5]  
Abbiati G, 2002, SYNTHESIS-STUTTGART, P1912
[6]   Rh-catalyzed sequential hydroarylation/hydrovinylation-heterocyclization of β-(2-aminophenyl)-α,β-ynones with organoboron derivatives:: A new approach to functionalized quinolines [J].
Abbiati, Giorgio ;
Arcadi, Antonio ;
Marinelli, Fabio ;
Rossi, Ellsabetta ;
Verdecchia, Mirella .
SYNLETT, 2006, (19) :3218-3224
[7]   Sequential 1,3-Dipolar Cycloaddition of Nitrones to β-(2-Aminophenyl) α,β-Ynones and Cyclocondensation: A New Entry to the Isoxazolino[4,5-c]quinoline Ring [J].
Abbiati, Giorgio ;
Arcadi, Antonio ;
Marinelli, Fabio ;
Rossi, Elisabetta ;
Verdecchia, Mirella .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (07) :1027-1031
[8]   2,6-Disubstituted and 2,2,6-Trisubstituted Piperidines from Serine: Asymmetric Synthesis and Further Elaboration [J].
Acharya, Hukum P. ;
Clive, Derrick L. J. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5223-5233
[9]   Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex [J].
Adamo, Carlo ;
Amatore, Christian ;
Ciofini, Ilaria ;
Jutand, Anny ;
Lakmini, Hakim .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6829-6836
[10]  
Ager D.J., 2007, Handbook for Homogeneous Hydrogenation, V2, P745