Quinoxaline-2,3-dithiol in reactions with propargyl bromide and 1,3-dibromopropyne |
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Authors: | T. I. Yaroshenko V. N. Elokhina A. S. Nakhmanovich L. I. Larina T. N. Komarova S. V. Amosova |
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Affiliation: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia |
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Abstract: | Propargyl bromide with quinoxaline-2,3-dithiol in DMSO in the presence of K2CO3 affords 2,3-bis-(2-propynylsulfanyl)quinoxaline in good yield whereas in absolute methanol in the presence of sodium methoxide at 20°C a 1:2 mixture of 2,3-bis(2-propynylsulfanyl)quinoxaline and 3-(2-propynylsulfanyl)-2(1H)-quinoxalinethione is formed. Individual 3-(2-propynylsulfanyl)-2(1H)-quinoxalinethione was obtained by crystallization of this mixture from ether. The reaction of 1,3-dibromopropyne with quinoxaline-2,3-dithiol in ethanol in the presence of NaOH at heating results in 2-bromomethylidene-1,4-(3H)-dithiino[2,3-b]quinoxaline in 77% yield. Performing this reaction in methanol in the presence of sodium methoxide during long heating (16 h) led to 2,3-bis[(3-bromo-2-propynyl)sulfanyl]quinoxaline in 72% yield. |
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