Core-Modified Hexaphyrins; Characterization of Two- and Four-Ring Inverted 26 π Aromatic Macrocycles

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3531-3533

  Rath, Harapriya ^a   Anand, V G ^a   Sankar, J ^a   Venkatraman, S ^a   Chandrashekar, T K ^a   Joshi, Bhawani S ^b   Khetrapal, C L ^b   Schilde, Uwe ^c   Senge, Mathias O ^c  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b SANJAY GANDHI POSTGRADUATE INSTITUTE OF MEDICAL SCIENCES   (India)

^c UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; HEXAPHYRIN; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 0345687211     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035408q     Document Type: Article

References (14)

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2. (a) Gossauer, A. Bull. Soc. Chim. Belg. 1983, 92, 793-795.
3. (b) Charrière, R.; Jenny, T. A.; Rexhausen, H.; Gossauer, A. Heterocycles 1993, 36, 1561-1575.
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12. In a typical procedure, modified tripyrrane 7 (0.6 g, 1.25 mmol) was reacted with 8 (0.2 g, 1.25 mmol) in dry dichloromethane (250 mL) and stirred under a nitrogen atmosphere in the absence of light for 15 min. p-Tolyl sulphonic acid (0.11 g, 0.62 mmol) was added and stirring continued for 90 min. The reaction mixture was exposed to air, and chloranil (0.3 g, 1.25 mmol) was added; the reaction mixture was refluxed for 90 min on a preheated oil bath. The solvent was removed under reduced pressure. Upon purification by column chromatography with alumina (basic, grade III), a pink band eluted with 2:3 dichloromethane/petroleum ether, which on solvent evaporation afforded 9 as a dark green solid [120 mg, 8%].
13. Smith, K. M. In Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol.1, pp 1-44.
14. th July, 2003. DOI: 10.1021/ar020284n.