α-(3,7-Dioxa-r-1-azabicyclo[3.3.0]oct-c-5-ylmethoxy)-diazines.: Part 2:: Functionalisation via directed ortho-metallation and cross-coupling reactions

被引：6

作者：

Berghian, Camelia

Condamine, Eric

Ple, Nelly

Turck, Alain

Silaghi-Dumitrescu, Ioan

Maiereanu, Carmen

Darabantu, Mircea

机构：

[1] Univ Babes Bolyai, Dept Organ Chem, RO-400028 Cluj Napoca, Romania

[2] Univ Rouen, IRCOF, F-76131 Mont St Aignan, France

[3] Univ Babes Bolyai, Dept Inorgan Chem, RO-400028 Cluj Napoca, Romania

来源：

TETRAHEDRON | 2006年 / 62卷 / 31期

关键词：

diazines; oxazolidines; metallation; cross-coupling; NMR; chirality;

D O I：

10.1016/j.tet.2006.05.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The functionalisation of the title compounds via regioselective Directed ortho-Metallation (DoM) and cross-coupling reactions is studied. The compatibility of the 3,7-DiOxa-r-l-AzaBicyclo[3.3.0]Oct-c-5-ylmethoxy system (DOABO-CH2O) to typical reaction conditions is established. Its role as Directed ortho-Metallation Group (DoMG) is examined, including competition with classical DoMGs, chlorine and methoxy. The chelating ability of some functionalised terms such as DOABO-CH20 substituting chiral diarylmethanols and polyaza analogues of 2,6-terpyridine is discussed as intramolecular steric relationships determining configuration and aptitude to bind selectively transition metals, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7339 / 7354

页数：16

相关论文

共 28 条

[1] CORRELATION OF PROTON AND N-15 CHEMICAL-SHIFTS BY MULTIPLE QUANTUM NMR [J].

BAX, A ;

GRIFFEY, RH ;

HAWKINS, BL .

JOURNAL OF MAGNETIC RESONANCE, 1983, 55 (02) :301-315

[2] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].

BAX, A ;

SUMMERS, MF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094

[3] SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY [J].

BAX, A ;

SUBRAMANIAN, S .

JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) :565-569

[4] Synthesis of new polyaza heterocycles.: Part 42:: Diazines [J].

Darabantu, M ;

Boully, L ;

Turck, A ;

Plé, N .

TETRAHEDRON, 2005, 61 (11) :2897-2905

[5] 3,7-dioxa-1-azabicyclo[3.3.0]octanes substituted at the C-5 position -: From local to global stereochemistry [J].

Darabantu, M ;

Maiereanu, C ;

Silaghi-Dumitrescu, I ;

Toupet, L ;

Condamine, E ;

Ramondenc, Y ;

Berghian, C ;

Plé, G ;

Plé, N .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) :2644-2661

[6] Synthesis and stereochemistry of some 1,3-oxazolidine systems based on TRIS (α,α,α-trimethylolaminomethane) and related aminopolyols skeleton.: part 1:: (Di)spiro-1,3-oxazolidines [J].

Darabantu, M ;

Plé, G ;

Silaghi-Dumitrescu, I ;

Maiereanu, C ;

Turos, I ;

Silberg, IA ;

Mager, S .

TETRAHEDRON, 2000, 56 (23) :3785-3798

[7] Practical asymmetric synthesis of (S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione, a key intermediate for the synthesis of irinotecan and other camptothecin analogs [J].

Henegar, KE ;

Ashford, SW ;

Baughman, TA ;

Sih, JC ;

Gu, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6588-6597

[8] INVESTIGATION OF EXCHANGE PROCESSES BY 2-DIMENSIONAL NMR-SPECTROSCOPY [J].

JEENER, J ;

MEIER, BH ;

BACHMANN, P ;

ERNST, RR .

JOURNAL OF CHEMICAL PHYSICS, 1979, 71 (11) :4546-4553

[9] MECHANISMS OF THE PALLADIUM-CATALYZED COUPLINGS OF ACID-CHLORIDES WITH ORGANOTIN REAGENTS [J].

LABADIE, JW ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (19) :6129-6137

[10] Homocamptothecins:: Synthesis and antitumor activity of novel E-ring-modified camptothecin analogues [J].

Lavergne, O ;

Lesueur-Ginot, L ;

Rodas, FP ;

Kasprzyk, PG ;

Pommier, J ;

Demarquay, D ;

Prévost, G ;

Ulibarri, G ;

Rolland, A ;

Schiano-Liberatore, AM ;

Harnett, J ;

Pons, D ;

Camara, J ;

Bigg, DCH .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (27) :5410-5419