Porphotetramethenes (Calix[4]pyrroletetraquinomethides) from Oxidative N-Alkylation of Porphyrin Tetraphenols

Eduard Dolusic; Suzanne Toppet; Stefan Smeets; Luc Van Meervelt; Bernard Tinant; Wim Dehaen

Porphotetramethenes (Calix[4]pyrroletetraquinomethides) from Oxidative N-Alkylation of Porphyrin Tetraphenols

Eduard Dolusic, Suzanne Toppet, Stefan Smeets, Luc Van Meervelt, Bernard Tinant, Wim Dehaen

Namur Research Institute for Life Sciences

Research output: Contribution to conference › Poster

Abstract

Air oxidation of porphyrin tetraphenols under basic conditions followed by N-alkylation readily provides tetrapyrrole macrocycles, in which the pyrroles are conected by sp^2 centers (as shown in the figure), in good yields. The reaction conditions were optimized to influence the degree of this one-pot reaction with different alkylation reagents. A number of partially, as well as mixed, N-substituted products were prepared. The yields obtained for certain products are a significant improvement as compared to earlier experiments by Milgrom et al. [J. Heterocycl. Chem. 32, 97 - 101 (1995)]

Original language	English
Pages	5th Sigma-Aldrich Organic Synthesis Meeting, Abstracts, Spa, Belgium, 06.-07.12.2001, pp. 11-11
Number of pages	1
Publication status	Published - 2001
Event	5th Sigma-Aldrich Organic Synthesis Meeting - Spa, Belgium Duration: 6 Dec 2001 → …

Symposium

Symposium	5th Sigma-Aldrich Organic Synthesis Meeting
Country/Territory	Belgium
City	Spa
Period	6/12/01 → …

Keywords

tetrapyrrole
N-alkylation
porphyrin
porphotetramethene

1 Poster
1 Article

Porphotetramethenes with 1,3-alternate conformation of pyrrole rings from oxidative N-alkylation of porphyrin tetraphenols
Dolusic, E., Toppet, S., Smeets, S., Van Meervelt, L., Tinant, B. & Dehaen, W., 2003, In: Tetrahedron. 59, 3, p. 395-400 6 p.
Research output: Contribution to journal › Article › peer-review

Open Access
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Oxidative Alkylation of tetrakis(4-Hydroxyaryl)porphyrins
Dolusic, E., Smeets, S. & Dehaen, W., 2000, p. 4th Sigma-Aldrich Organic Synthesis Meeting, Abstracts, Spa, Belgium, 07.-08.12.2000. 1 p.
Research output: Contribution to conference › Poster

2 Participation in conference

5th Sigma-Aldrich Organic Synthesis Meeting
Dolusic, E. (Poster)
6 Dec 2001 → 7 Dec 2001
Activity: Participating in or organising an event types › Participation in conference
4th Sigma-Aldrich Organic Synthesis Meeting
Dolusic, E. (Poster)
7 Dec 2000 → 8 Dec 2000
Activity: Participating in or organising an event types › Participation in conference

PhD in organic chemistry Katholieke Universiteit Leuven, Belgium, 2000 - 2004 (Prof. Wim Dehaen)
Dolusic, E. (Author), 2004
Student thesis: Doc types › Doctor of Sciences

Cite this

Dolusic, E., Toppet, S., Smeets, S., Van Meervelt, L., Tinant, B., & Dehaen, W. (2001). Porphotetramethenes (Calix[4]pyrroletetraquinomethides) from Oxidative N-Alkylation of Porphyrin Tetraphenols. 5th Sigma-Aldrich Organic Synthesis Meeting, Abstracts, Spa, Belgium, 06.-07.12.2001, pp. 11-11. Poster session presented at 5th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium.

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title = "Porphotetramethenes (Calix[4]pyrroletetraquinomethides) from Oxidative N-Alkylation of Porphyrin Tetraphenols",

abstract = "Air oxidation of porphyrin tetraphenols under basic conditions followed by N-alkylation readily provides tetrapyrrole macrocycles, in which the pyrroles are conected by sp^2 centers (as shown in the figure), in good yields. The reaction conditions were optimized to influence the degree of this one-pot reaction with different alkylation reagents. A number of partially, as well as mixed, N-substituted products were prepared. The yields obtained for certain products are a significant improvement as compared to earlier experiments by Milgrom et al. [J. Heterocycl. Chem. 32, 97 - 101 (1995)]",

keywords = " tetrapyrrole, N-alkylation, porphyrin, porphotetramethene",

author = "Eduard Dolusic and Suzanne Toppet and Stefan Smeets and {Van Meervelt}, Luc and Bernard Tinant and Wim Dehaen",

year = "2001",

language = "English",

pages = "5th Sigma--Aldrich Organic Synthesis Meeting, Abstracts, Spa, Belgium, 06.--07.12.2001, pp. 11--11",

note = "5th Sigma-Aldrich Organic Synthesis Meeting ; Conference date: 06-12-2001",

}

Porphotetramethenes (Calix[4]pyrroletetraquinomethides) from Oxidative N-Alkylation of Porphyrin Tetraphenols. / Dolusic, Eduard; Toppet, Suzanne; Smeets, Stefan et al.
2001. 5th Sigma-Aldrich Organic Synthesis Meeting, Abstracts, Spa, Belgium, 06.-07.12.2001, pp. 11-11 Poster session presented at 5th Sigma-Aldrich Organic Synthesis Meeting, Spa, Belgium.

Research output: Contribution to conference › Poster

TY - CONF

T1 - Porphotetramethenes (Calix[4]pyrroletetraquinomethides) from Oxidative N-Alkylation of Porphyrin Tetraphenols

AU - Dolusic, Eduard

AU - Toppet, Suzanne

AU - Smeets, Stefan

AU - Van Meervelt, Luc

AU - Tinant, Bernard

AU - Dehaen, Wim

PY - 2001

Y1 - 2001

N2 - Air oxidation of porphyrin tetraphenols under basic conditions followed by N-alkylation readily provides tetrapyrrole macrocycles, in which the pyrroles are conected by sp^2 centers (as shown in the figure), in good yields. The reaction conditions were optimized to influence the degree of this one-pot reaction with different alkylation reagents. A number of partially, as well as mixed, N-substituted products were prepared. The yields obtained for certain products are a significant improvement as compared to earlier experiments by Milgrom et al. [J. Heterocycl. Chem. 32, 97 - 101 (1995)]

AB - Air oxidation of porphyrin tetraphenols under basic conditions followed by N-alkylation readily provides tetrapyrrole macrocycles, in which the pyrroles are conected by sp^2 centers (as shown in the figure), in good yields. The reaction conditions were optimized to influence the degree of this one-pot reaction with different alkylation reagents. A number of partially, as well as mixed, N-substituted products were prepared. The yields obtained for certain products are a significant improvement as compared to earlier experiments by Milgrom et al. [J. Heterocycl. Chem. 32, 97 - 101 (1995)]

KW - tetrapyrrole

KW - N-alkylation

KW - porphyrin

KW - porphotetramethene

M3 - Poster

SP - 5th Sigma-Aldrich Organic Synthesis Meeting, Abstracts, Spa, Belgium, 06.-07.12.2001, pp. 11-11

T2 - 5th Sigma-Aldrich Organic Synthesis Meeting

Y2 - 6 December 2001

ER -

Porphotetramethenes (Calix[4]pyrroletetraquinomethides) from Oxidative N-Alkylation of Porphyrin Tetraphenols

Abstract

Symposium

Keywords

Fingerprint

Research output

Porphotetramethenes with 1,3-alternate conformation of pyrrole rings from oxidative N-alkylation of porphyrin tetraphenols

Oxidative Alkylation of tetrakis(4-Hydroxyaryl)porphyrins

Activities

5th Sigma-Aldrich Organic Synthesis Meeting

4th Sigma-Aldrich Organic Synthesis Meeting

Student theses

PhD in organic chemistry Katholieke Universiteit Leuven, Belgium, 2000 - 2004 (Prof. Wim Dehaen)

Cite this