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New Triazinoindoles through the Action of 3-Hydrazino[1,2,4]triazino[5,6-b]indole on α,β-Unsaturated Compounds

Ahmed S. A. Youssef

Department of Chemistry, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt

 

E-mail: ahmedy67@hotmail.com

Received: 16 November 2000  Accepted: 24 July 2001

Abstract: 3-Hydrazino[1,2,4]triazino[5,6-b]indole (I) reacted with 1-aryl-3-phenylprop-2-yn-1-ones IIa—IIc to give 3-(5-aryl-3-phenylpyrazol-1-yl)[l,2,4]triazino[5,6-b]indoles IIIa—IIIc. ω-(p-Chlorobenzoyl)acetophenone ([1,2,4]triazino[5,6-b]indol)-3-ylhydrazone was isolated in case of IIb only. On the other hand, methyl (p-chlorophenyl)prop-2-ynoate (IId) gave 3-[3-(p-chlorophenyl)-5-hydroxypyrazol-1- yl][1,2,4]triazino[5,6-b]indole (IIId). I reacted with diethyl but-2-ynedioate to give 3-((4H)-3- ethoxycarbonyl-5-oxopyrazol-1-yl)[1,2,4]triazino[5,6-b]indole and diethyl oxaloacetate ([1,2,4]triazino[ 5,6-b]indol)-3-ylhydrazone. Similar treatment of I with 2-cyano- or 2-cyano-3-methylcinnamonitriles afforded 3-((4H)-3,5-dioxo-4-phenylmethylenepyrazol-2-yl)- and 3-[(4H)-3,5-dioxo-4-(1-phenylethylene) pyrazol-2-yl][1,2,4]triazino[5,6-b]indoles, respectively. Structures of all products are evidenced by microanalytical and spectral data.

Full paper in Portable Document Format: 562a132.pdf

 

Chemical Papers 56 (2) 132–137 (2002)

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