Synthesis and transformations of 1,4-diethynyl-2-nitrobenzene |
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| Authors: | D. L. Tarshits S. Yu. Tarasov V. N. Buyanov |
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| Affiliation: | (1) Moscow Department of Education, Moscow Institute of Open Education, 6 Aviatsionnyi pr., 125167 Moscow, Russian Federation;(2) Research and Production Center “Farmzashchita” of the Federal Agency “Medbioextrem”, 11 Vashutinskoe shosse, Khimki, 141400, Russian Federation;(3) D. I. Mendeleev Russian University of Chemical Technology, 9 Miusskaya ploshchad’, 125047 Moscow, Russian Federation |
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| Abstract: | Heating 2-nitro-1,4-bis(1,3,3-trimethylindolin-2-ylideneacetyl)benzene with POCl3 followed by treatment with an aqueous solution of NaOH gave 2-nitro-1,4-diethynylbenzene. Some transformations involving this product were considered. 2-Acetylamino-1,4-diethynylbenzene and its dimorpholinomethyl derivative underwent heterocyclization, resulting in the terminal and methine carbon-substituted indolylacetylenes. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2505–2508, November, 2005. |
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| Keywords: | acetylene fragmentation indoline enaminoketones Fischer base 2-nitro-1,4-diethynylbenzene aminomethylation heterocyclization 6-ethynylindole |
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