Synthesis of phenazine derivatives for use as precursors to electrochemically generated bases

被引：17

作者：

Alonso, AM ^{[1
]}

Horcajada, R ^{[1
]}

Groombridge, HJ ^{[1
]}

Chudasama, R ^{[1
]}

Motevalli, M ^{[1
]}

Utley, JHP ^{[1
]}

Wyatt, PB ^{[1
]}

机构：

[1] Univ London, Dept Chem, London E1 4NS, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 15期

关键词：

D O I：

10.1039/b506295k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,6-Disubstituted phenazine derivatives for use as precursors to electrochemically generated bases have been synthesized from readily available starting materials. Reaction of 1,6- dihydroxyphenazine with 1,10-diododecane, 1,11-diiodo-3,6,9-trioxaundecane or (R,R)-(-)-1,2-bis(3-iodopropoxy) cyclohexane gave planar chiral phenazinophanes containing ether-linked bridges; molecular structures of all these compounds have been determined by X-ray crystallography. Substituted 1,6-diaminophenazines were prepared by palladium-mediated amination of 1,6-dichlorophenazine and acylation of 1,6- diaminophenazine followed by reduction. Reaction of 1,6-bis-(alkylamino)phenazines with sebacoyl chloride gave planar chiral phenazinophanes containing amide-linked bridges.

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页码：2832 / 2841

页数：10

相关论文

共 12 条

[1] The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation [J].

Alonso, AM ;

Horcajada, R ;

Motevalli, M ;

Utley, JHP ;

Wyatt, PB .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (15) :2842-2847

[2] Generation of strong, homochiral bases by electrochemical reduction of phenazine derivatives [J].

Alonso, AM ;

Horcajada, R ;

Groombridge, HJ ;

Mandalia, R ;

Motevalli, M ;

Utley, JHP ;

Wyatt, PB .

CHEMICAL COMMUNICATIONS, 2004, (04) :412-413

[3] Kinetics of proton transfer from phosphonium ions to electrogenerated bases: polar, steric and structural influences on kinetic acidity and basicity [J].

Bettencourt, AP ;

Freitas, AM ;

Montenegro, MI ;

Nielsen, MF ;

Utley, JHP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (03) :515-522

[4] C-13 NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF SUBSTITUTED PHENAZINES [J].

BREITMAIER, E ;

HOLLSTEIN, U .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2104-2108

[5] DNMR AND MOLECULAR MECHANICS STUDIES OF THE ENANTIOMERIZATION OF LONG-CHAIN (1,5)-NAPHTHALENOPHANES [J].

CHANG, MH ;

MASEK, BB ;

DOUGHERTY, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1124-1133

[6]

COOPER GF, 1991, SYNTHESIS-STUTTGART, P859

[7] CHIRAL CROWN ETHERS DERIVED FROM (+)-(1S, 2S)-TRANS-CYCLOHEXANE-1,2-DIOL [J].

HAYWARD, RC ;

OVERTON, CH ;

WHITHAM, GH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (22) :2413-2415

[8] Synthesis of novel acridino- and phenazino-18-crown-6 ligands and their optically pure dimethyl-substituted analogues for molecular recognition studies [J].

Huszthy, P ;

Samu, E ;

Vermes, B ;

Mezey-Vándor, G ;

Nógrádi, M ;

Bradshaw, JS ;

Izatt, RM .

TETRAHEDRON, 1999, 55 (05) :1491-1504

[9] Enantioselective catalytic ring opening of epoxides with carboxylic acids [J].

Jacobsen, EN ;

Kakiuchi, F ;

Konsler, RG ;

Larrow, JF ;

Tokunaga, M .

TETRAHEDRON LETTERS, 1997, 38 (05) :773-776

[10] PHOTORESPONSIVE SUPRAMOLECULAR SYSTEMS - SYNTHESIS AND PHOTOPHYSICAL AND PHOTOCHEMICAL STUDY OF BIS-(9,10-ANTHRACENEDIYL)CORANANDS AAO(N)O(N) [J].

MARQUIS, D ;

DESVERGNE, JP ;

BOUASLAURENT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7984-7996