Intramolecular Oxidative Pd(II)-Catalyzed Alkoxylation of 3-Aza-5-alkenols with O2 as Sole Oxidant: Mild Conditions for the Synthesis of 1,4-Oxazine Derivatives

被引：19

作者：

Broggini, Gianluigi ^{[1
]}

Beccalli, Egle M. ^{[2
]}

Borsini, Elena ^{[2
]}

Fasana, Andrea ^{[1
]}

Zecchi, Gaetano ^{[1
]}

机构：

[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

[2] Univ Milan, DISMAB, Sez Chim Organ A Marchesini, I-20133 Milan, Italy

来源：

SYNLETT | 2011年 / 02期

关键词：

palladium; heterocycles; alkenols; alkoxylation; molecular oxygen; C-H ACTIVATION; WACKER-TYPE CYCLIZATION; MOLECULAR-OXYGEN; CATALYZED CYCLIZATION; INDOLE-DERIVATIVES; HYDROGEN-PEROXIDE; TERMINAL ALKENES; PALLADIUM; AMINATION; BOND;

D O I：

10.1055/s-0030-1259295

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 1,4-2H-oxazine derivatives was performed by Pd(II)-catalyzed aerobic oxidative cyclization of 3-aza-5-alkenols, prepared from easily available 1,2-amino alcohols. The reaction proceeds in very mild conditions with a simple catalytic system consisting of PdCl2(MeCN)(2) in THF at room temperature with molecular oxygen as the sole stoichiometric oxidant.

引用

收藏

页码：227 / 230

页数：4

相关论文

共 70 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] Regioselectivity on the palladium-catalyzed intramolecular cyclization of indole derivatives [J].

Abbiati, G ;

Beccalli, EM ;

Broggini, G ;

Zoni, C .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7625-7628

[3] Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives [J].

Achari, B ;

Mandal, SB ;

Dutta, PK ;

Chowdhury, C .

SYNLETT, 2004, (14) :2449-2467

[4] 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

[5] Palladium-Catalyzed Dehydrogenative Coupling of Furans with Styrenes [J].

Aouf, Chahinez ;

Thiery, Emilie ;

Le Bras, Jean ;

Muzart, Jacques .

ORGANIC LETTERS, 2009, 11 (18) :4096-4099

[6] Intramolecular Pd(II)-catalyzed cyclization of propargylamides: Straightforward synthesis of 5-oxazolecarbaldehydes [J].

Beccalli, Egle M. ;

Borsini, Elena ;

Broggini, Gianluigi ;

Palmisano, Giovanni ;

Sottocornola, Silvia .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4746-4749

[7] 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

[8] 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

[9] Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines [J].

Beccalli, EM ;

Broggini, G ;

Martinelli, M ;

Paladino, G .

TETRAHEDRON, 2005, 61 (05) :1077-1082

[10] Regioselective formation of six- and seven-membered ring by intramolecular Pd-catalyzed amination of N-allyl-anthranilamides [J].

Beccalli, EM ;

Broggini, G ;

Paladino, G ;

Penoni, A ;

Zoni, C .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5627-5630

← 1 2 3 4 5 6 7 →