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

Ofir Arad; Jordi Morros; Xavier Batllori; Jordi Teixidó; Santiago Nonell; José I. Borrell

doi:10.1021/ol052913+

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

Ofir Arad
, Jordi Morros
, Xavier Batllori
, Jordi Teixidó
, Santiago Nonell
, José I. Borrell^*

^*Corresponding author for this work

IQS School of Engineering

Research output: Indexed journal article › Article › peer-review

34 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	847-850
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	5
DOIs	https://doi.org/10.1021/ol052913+
Publication status	Published - 2 Mar 2006

Keywords

Photodynamic therapy
Photosensitizing properties
Heterocyclic series
In-vitro
Porphycene
Cells
Tetraphenylporphycene
Carcinoma
2,7,12,17-tetraphenylporphycene

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title = "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",

abstract = "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.",

keywords = "Photodynamic therapy, Photosensitizing properties, Heterocyclic series, In-vitro, Porphycene, Cells, Tetraphenylporphycene, Carcinoma, 2,7,12,17-tetraphenylporphycene",

author = "Ofir Arad and Jordi Morros and Xavier Batllori and Jordi Teixid{\'o} and Santiago Nonell and Borrell, \{Jos{\'e} I.\}",

year = "2006",

month = mar,

day = "2",

doi = "10.1021/ol052913+",

language = "English",

volume = "8",

pages = "847--850",

journal = "Organic Letters",

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T1 - Diethyl 2,7-dibromo-4H,5H-thieno[3,2-b:4,5-b′]dipyrrole-3,6- dicarboxylate

T2 - A key intermediate for a diversity oriented synthesis of 2,7,12,17-tetraarylporphycenes

AU - Arad, Ofir

AU - Morros, Jordi

AU - Batllori, Xavier

AU - Teixidó, Jordi

AU - Nonell, Santiago

AU - Borrell, José I.

PY - 2006/3/2

Y1 - 2006/3/2

N2 - 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.

AB - 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.

KW - Photodynamic therapy

KW - Photosensitizing properties

KW - Heterocyclic series

KW - In-vitro

KW - Porphycene

KW - Cells

KW - Tetraphenylporphycene

KW - Carcinoma

KW - 2,7,12,17-tetraphenylporphycene

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DO - 10.1021/ol052913+

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ER -

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

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Keywords

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