Diethyl 2,7-dibromo-4H,5H-thieno[3,2-b:4,5-b′]dipyrrole-3,6-dicarboxylate:: A key intermediate for a diversity oriented synthesis of 2,7,12,17-tetraarylporphycenes

被引：32

作者：

Arad, O ^{[1
]}

Morros, J ^{[1
]}

Batllori, X ^{[1
]}

Teixidó, J ^{[1
]}

Nonell, S ^{[1
]}

Borrell, JI ^{[1
]}

机构：

[1] Univ Ramon Llull, Inst Quim Sarria, Grp Engn Mol, E-08017 Barcelona, Spain

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 05期

关键词：

D O I：

10.1021/ol052913+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new Suzuki-based strategy for the synthesis of 4,4'-diaryl (or heteroaryl)-substituted 2,2'-bipyrroles (10), precursors of 2,7,12,17-tetraaryl (or heteroaryl)-substituted porphycenes, is described. Bromination of the previously described diethyl 4H,5H-thieno[3,2-b:4,5-b']dipyrrole-3,6-dicarboxylate afforded dibromo compound 19, which is the key intermediate of such strategy.

引用

页码：847 / 850

页数：4

共 26 条

[1] PHOTODYNAMIC THERAPY OF HUMAN BLADDER-CARCINOMA CELLS IN-VITRO WITH PH-SENSITIVE LIPOSOMES AS CARRIERS FOR 9-ACETOXY-TETRA-N-PROPYLPORPHYCENE [J].

AICHER, A ;

MILLER, K ;

REICH, E ;

HAUTMANN, R .

UROLOGICAL RESEARCH, 1994, 22 (01) :25-32

[2] Steric and electronic effects in methyl-substituted 2,2′-bipyrroles and poly(2,2′-bipyrrole)s:: Part I.: Synthesis and characterization of monomers and polymers [J].

Benincori, T ;

Brenna, E ;

Sannicolò, F ;

Zotti, G ;

Zecchin, S ;

Schiavon, G ;

Gatti, C ;

Frigerio, G .

CHEMISTRY OF MATERIALS, 2000, 12 (05) :1480-1489

[3]

Cañete M, 2000, ANTI-CANCER DRUG DES, V15, P143

[4]

Cañete M, 2004, INT J ONCOL, V24, P1221

[5]

Canete M, 1997, ANTI-CANCER DRUG DES, V12, P543

[6] HETEROCYCLIC SERIES .28. DIPYRROLE SYNTHESIS [J].

FARNIER, M ;

SOTH, S ;

FOURNARI, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (07) :1083-1086

[7] HETEROCYCLIC SERIES .27. CONDENSATION OF ETHYL AZIDOACETATE ON THIOPHENE-2,5-DICARBALDEHYDES, THIOPHENE-2,4-DICARBALDEHYDE AND THIOPHENE-3,4-DICARBALDEHYDE [J].

FARNIER, M ;

SOTH, S ;

FOURNARI, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (07) :1074-1082

[8]

FERINGA BL, 1988, SYNTHESIS-STUTTGART, P316

[9] A non-tetradecarboxylative synthesis of 2,7,12,17-tetraphenylporphycene [J].

Gavalda, A ;

Borrell, JI ;

Teixido, J ;

Nonell, S ;

Arad, O ;

Grau, R ;

Cañete, MC ;

Juarranz, A ;

Villanueva, A ;

Stockert, JC .

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2001, 5 (12) :846-852

[10] Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues [J].

Ghosez, L ;

Franc, C ;

Denonne, F ;

Cuisinier, C ;

Touillaux, R .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (11) :1827-1839

← 1 2 3 →