Novel Aspects of Domino Reaction of Indoles with Homo- Phthalaldehyde and Tere-phthalaldehyde

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Mardia T. El Sayed
Mardia T. El Sayed PhD
σ
Khadiga M. Ahmed
Khadiga M. Ahmed
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Kazem Mahmoud
Kazem Mahmoud
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Andreas Hilgeroth
Andreas Hilgeroth
α National Research Centre

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Novel Aspects of Domino Reaction of Indoles with  Homo-  Phthalaldehyde and Tere-phthalaldehyde

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Abstract

In the present work domino reaction of indole with homophthaladehyde (1) have been investigated for the first time. The reaction have been done in presence of glacial acetic acid as catalyst and solvent afford the novel un probable mixture of two isomers A and B of benzo[7]anulene (2) that couldn’t be divided accompany with the formation of the predictable tetraindole (3) in a yield of 46 to 38 % respectively. Terephthaladehyde (4) condensed with indoles in glacial acetic acid in a molar ratio (1:4) affording compounds 5 a,b in a high yield of 93 -95 % after a short time of stirring at room temperature. Compounds 5 a,b can act as nucleophile due to the unoccupied two positions of the four indole rings. Accordingly we now present for the first time a expedient method for the synthesis of the novel extensive ring systems 6 and (7 a-f ) via condensation reaction of compound 5 a with aryl or heteroaryl substituted aldehydes in a molar ratio (1:2).

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Funding

No external funding was declared for this work.

Conflict of Interest

The authors declare no conflict of interest.

Ethical Approval

No ethics committee approval was required for this article type.

Data Availability

Not applicable for this article.

How to Cite This Article

Mardia T. El Sayed. 2014. \u201cNovel Aspects of Domino Reaction of Indoles with Homo- Phthalaldehyde and Tere-phthalaldehyde\u201d. Global Journal of Science Frontier Research - B: Chemistry GJSFR-B Volume 14 (GJSFR Volume 14 Issue B6): .

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GJSFR Volume 14 Issue B6
Pg. 15- 21
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Crossref Journal DOI 10.17406/GJSFR

Print ISSN 0975-5896

e-ISSN 2249-4626

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December 18, 2014

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In the present work domino reaction of indole with homophthaladehyde (1) have been investigated for the first time. The reaction have been done in presence of glacial acetic acid as catalyst and solvent afford the novel un probable mixture of two isomers A and B of benzo[7]anulene (2) that couldn’t be divided accompany with the formation of the predictable tetraindole (3) in a yield of 46 to 38 % respectively. Terephthaladehyde (4) condensed with indoles in glacial acetic acid in a molar ratio (1:4) affording compounds 5 a,b in a high yield of 93 -95 % after a short time of stirring at room temperature. Compounds 5 a,b can act as nucleophile due to the unoccupied two positions of the four indole rings. Accordingly we now present for the first time a expedient method for the synthesis of the novel extensive ring systems 6 and (7 a-f ) via condensation reaction of compound 5 a with aryl or heteroaryl substituted aldehydes in a molar ratio (1:2).

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Novel Aspects of Domino Reaction of Indoles with Homo- Phthalaldehyde and Tere-phthalaldehyde

Mardia T. El Sayed
Mardia T. El Sayed National Research Centre
Khadiga M. Ahmed
Khadiga M. Ahmed
Kazem Mahmoud
Kazem Mahmoud
Andreas Hilgeroth
Andreas Hilgeroth

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