Intra-Intermolecular Palladium-Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones

被引：23
作者：
Broggini, Gianluigi [1 ]
Beccalli, Egle M. [2 ]
Borelli, Tea [1 ]
Brusa, Filippo [1 ]
Gazzola, Silvia [1 ]
Mazza, Alberto [2 ]
机构：
[1] Univ Insubria, Dipartimento Sci & Alta Tecnol, I-22100 Como, Italy
[2] Univ Milan, DISMAB, Sez Chim Organ A Marchesini, I-20133 Milan, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 19期
关键词：
Homogeneous catalysis; Palladium; Domino reactions; Amination; Nitrogen heterocycles; B1 RECEPTOR ANTAGONISTS; INTRAMOLECULAR DIAMINATION; C-H; ALKENES; CYCLIZATION; POTENT; ACID; INHIBITORS; DISCOVERY; ESTERS;
D O I：
10.1002/ejoc.201500386
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Easily accessible N-tosylglycine allylamides have been converted into diversely functionalized piperazinone derivatives by inter-intramolecular oxidative domino palladium-catalyzed reactions. Aminochlorination and aminoacetoxylation processes were achieved by employing CuCl2 and PhI(OAc)(2) as the oxidizing agents to give 5-chloromethyl- and 5-acetoxymethyl-substituted piperazinones, respectively.
引用
收藏
页码：4261 / 4268
页数：8
相关论文
共 69 条
[1]   Pd-catalyzed cyclization of 1-allyl-2-indolecarboxamides by intramolecular amidation of unactivated ethylenic bond [J].
Abbiati, G ;
Beccalli, E ;
Broggini, G ;
Martinelli, M ;
Paladino, G .
SYNLETT, 2006, (01) :73-76
[2]   Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences [J].
Alcaide, B ;
Almendros, P ;
Rodríguez-Acebes, R .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2346-2351
[3]   Pd-Cu bimetallic catalyzed domino cyclization of α-allenols followed by a coupling reaction:: New sequence leading to functionalized spirolactams [J].
Alcaide, B ;
Almendros, P ;
Rodríguez-Acebes, R .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (19) :5708-5712
[4]   Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].
Alexanian, EJ ;
Lee, C ;
Sorensen, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691
[5]   Palladium-Catalyzed Cyclization of Unsaturated β-Amino Alcohols: A New Access to Enantiopure Bicyclic Oxazolidines [J].
Alladoum, Jeanne ;
Vrancken, Emmanuel ;
Mangeney, Pierre ;
Roland, Sylvain ;
Kadouri-Puchot, Catherine .
ORGANIC LETTERS, 2009, 11 (16) :3746-3749
[6]   Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions [J].
Aparicio, Domitila ;
Attanasi, Orazio A. ;
Filippone, Paolino ;
Ignacio, Roberto ;
Lillini, Samuele ;
Mantellini, Fabio ;
Palacios, Francisco ;
Santos, Jesus M. de los .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :5897-5905
[7]   Novel bicyclisation of unsaturated polyols in PdCl2-CuCl2-AcOH catalytic system [J].
Babjak, M ;
Remen, L ;
Szolcsányi, P ;
Zálupsky, P ;
Miklos, D ;
Gracza, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (05) :928-940
[8]   Synthesis of tetrahydrofurans through a novel pseudo-meso-trick [J].
Babjak, M ;
Remen, L ;
Karlubíková, O ;
Gracza, T .
SYNLETT, 2005, (10) :1609-1611
[9]   Intramolecular palladium-catalyzed oxidative coupling on thiophene and furan rings: Determinant role of the electronic availability of the heterocycle [J].
Beccalli, Egle M. ;
Borsini, Elena ;
Broggini, Gianluigi ;
Rigamonti, Micol ;
Sottocornola, Silvia .
SYNLETT, 2008, (07) :1053-1057
[10]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
1234567