Reaction of 3-Arylaminobenzofuro-, 3-Arylaminobenzothieno-, and 3-Arylaminoindolo[2,3-<Emphasis Type="Italic">c</Emphasis>]pyrylium Salts with Nucleophilic Reagents |
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| Authors: | V S Tolkunov Yu B Vysotsky O A Gorban’ S V Shishkina O V Shishkin V I Dulenko |
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| Institution: | (1) L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk, 83114, Ukraine;(2) Donbass State Academy of Construction and Architecture, Makeevka, 86128, Ukraine;(3) Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkov, 310001, Ukraine |
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| Abstract: | We have studied the reactions of 3-arylaminobenzofuro-, 3-arylaminobenzothieno-, and 3-arylaminoindolo2,3-c]pyrylium salts with ammonium acetate, primary amines, and hydrazine hydrate. In an alcoholic medium, primary amines and hydrazine hydrate open up the pyrylium ring to form arylamides of 2-(N-benzylmethylketimine)hetaryl-3-acetic acids or the corresponding hydrazones, where further heterocyclization does not occur. Upon treatment with ammonium acetate in acetic acid, 2-aryl-1-methylhetero2,3-c]pyridin-3-(2H)-ones are formed along with their 2-unsubstituted analogs.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 601–612, April, 2005. |
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| Keywords: | 3-arylaminobenzothieno[2 3-c]pyrylium 3-arylaminobenzofuro[2 3-c]pyrylium 3-arylaminoindolo[2 3-c]pyrylium 2-N-aryl-1-methylhetero[2 3-c]pyridin-3(2H)-ones recyclization |
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