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Vol. 25 No. 15 (2013): Vol 25 Issue 15

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Facile Synthesis of Substituted 3-(1-Ethyl-1H-indol-3-yl)-2-(1-methyl-1H-indole- 3-carbonyl)acrylonitrile and Their Antimicrobial Activities

https://doi.org/10.14233/ajchem.2013.15382
G. Thirupathi
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500 085, India
M. Venkatanarayana
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500 085, India
P.K. Dubey
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500 085, India
Y. Bharathi Kumari
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : G. Thirupathi

thirupathigjntuh@gmail.com

Asian Journal of Chemistry, Vol. 25 No. 15 (2013): Vol 25 Issue 15

Abstract

Facile syntheses of substituted 3-(1-methyl-1H-indol-3-yl)-2-(1-ethyl-1H-indole-3-carbonyl)acrylonitriles 5(a-d) is being reported. L-Tyrosine has been utilized as an efficient and eco-friendly catalyst in water at room temperature for Knoevenagel condensation of N-ethyl indole-3-carboxyaldehyde (2) with 3-cyanoacetylindole contain active methylene group 3(a-d), at room temperature to afford substituted 3-(1-ethyl-1H-indol-3-yl)-2-(1H-indole-3- carbonyl)acrylonitrile 4(a-d), respectively. Subsequently these products were treated with dimethyl sulfate in the presence of Na2CO3 as a base and triethyl benzylammonium chloride (TEBAC) as phase transfer catalyst in DMF at room temperature for 1 h to afford the corresponding substituted 3-(1-ethyl-1H-indol-3-yl)-2-(1-methyl-1H-indole-3-carbonyl)acrylonitrile 5(a-d). The antibacterial and antifungal activities of 4(a-d) and 5(a-d) have been studied.

Keywords

Indole-3-carboxyaldehyde 3-Cyanoacetylindole L-Tyrosine Water
Thirupathi, G., Venkatanarayana, M., Dubey, P., & Bharathi Kumari, Y. (2013). Facile Synthesis of Substituted 3-(1-Ethyl-1H-indol-3-yl)-2-(1-methyl-1H-indole- 3-carbonyl)acrylonitrile and Their Antimicrobial Activities. Asian Journal of Chemistry, 25(15), 8749–8754. https://doi.org/10.14233/ajchem.2013.15382
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