Synthesis of meso-tetraphenylthiaporphyrins bearing one inverted pyrrole

被引：59

作者：

Lee, CH

Kim, HJ

机构：

[1] Department of Chemistry, Kangwon National University

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(97)00783-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aza-21-thia-23-carba-5,10,15,20-tetraphenylporphyrin and its N-methylated analogue were synthesized and characterized. The synthesis utilizes [3+1] condensation of thiatripyrrin with 2,4-bis(alpha-hydroxy-alpha-phenylmethyl)pyrrole or 2,4-bis(alpha-hydroxy-alpha-phenylmethyl)-N-methylpyrrole in the presence of acid catalyst. This convenient process gives predominently the titled porphyrin. Reinversion of the pyrrole unit is observed by prolonging the reaction time. (C) 1997 Elsevier Science Ltd.

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页码：3935 / 3938

页数：4

相关论文

共 14 条

[1] Specific binding of iodide ion to N-confused tetraphenylporphyrin (NC-TPP) at the air-water interface [J].

Ariga, K ;

Kunitake, T ;

Furuta, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (04) :667-672

[2]

BERLIN K, 1994, ANGEW CHEM INT EDIT, V33, P219, DOI 10.1002/anie.199402191

[3] TETRA-P-TOLYLPORPHYRIN WITH AN INVERTED PYRROLE RING - A NOVEL ISOMER OF PORPHYRIN [J].

CHMIELEWSKI, PJ ;

LATOSGRAZYNSKI, L ;

RACHLEWICZ, K ;

GLOWIAK, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (07) :779-781

[4]

CHMIELEWSKI PJ, 1994, ANGEW CHEM, V106, P805

[5] NOVEL PORPHYRINOIDS FOR CHEMISTRY AND MEDICINE BY BIOMIMETIC SYNTHESES [J].

FRANCK, B ;

NONN, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1795-1811

[6]

FURATA H, 1994, J AM CHEM SOC, V116, P767

[7] 21-THIATETRA-PARA-TOLYLPORPHYRIN AND ITS COPPER(II) BICARBONATE COMPLEX - STRUCTURAL EFFECTS OF COPPER THIOPHENE BINDING [J].

LATOSGRAZYNSKI, L ;

LISOWSKI, J ;

OLMSTEAD, MM ;

BALCH, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4428-4429

[8] Stepwise syntheses of core-modified, meso-substituted porphyrins [J].

Heo, PY ;

Shin, K ;

Lee, CH .

TETRAHEDRON LETTERS, 1996, 37 (02) :197-200

[9]

HEO PY, 1996, B KOR CHEM SOC, V117, P778

[10] ONE-FLASK SYNTHESIS OF MESOSUBSTITUTED DIPYRROMETHANES AND THEIR APPLICATION IN THE SYNTHESIS OF TRANS-SUBSTITUTED PORPHYRIN BUILDING-BLOCKS [J].

LEE, CH ;

LINDSEY, JS .

TETRAHEDRON, 1994, 50 (39) :11427-11440