Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation

Verfasser / Beitragende:
[N. Tsizorik, A. Vas'kevich, R. Vas'kevich, M. Vovk]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/2(2015-02-01), 226-230
Format:
Artikel (online)
ID: 605531099
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024 7 0 |a 10.1134/S1070428015020165  |2 doi 
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245 0 0 |a Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation  |h [Elektronische Daten]  |c [N. Tsizorik, A. Vas'kevich, R. Vas'kevich, M. Vovk] 
520 3 |a Cinnamylacetamides reacted with arylsulfenyl chlorides in chloroform in the absence of LiClO4 affording 5-(arylsulfanyl)-6-phenylpiperidin-2-ones. Their reduction with a system LiAlH4-AlCl3 resulted in 3-(tolylsulfanyl)-1,2-diphenylpiperidine, and with Raney nickel, in 1-aryl-6-phenylpiperidin-2-ones. The latter treated with LiAlH4-AlCl3 were converted into 1-aryl-2-phenyl-piperidines. The oxidation of 5-(arylsulfanyl)-6-phenylpiperidin-2-ones with hydrogen peroxide in acetone led to the formation of 5-sulfinyl-, and with oxone, to 5-sulfonyl derivatives. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Tsizorik  |D N.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine  |4 aut 
700 1 |a Vas'kevich  |D A.  |u National Technical University of Ukraine "KPI”, pr. Pobedy 37, 03056, Kiev, Ukraine  |4 aut 
700 1 |a Vas'kevich  |D R.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine  |4 aut 
700 1 |a Vovk  |D M.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/2(2015-02-01), 226-230  |x 1070-4280  |q 51:2<226  |1 2015  |2 51  |o 11178 
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950 |B NATIONALLICENCE  |P 700  |E 1-  |a Tsizorik  |D N.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Vas'kevich  |D A.  |u National Technical University of Ukraine "KPI”, pr. Pobedy 37, 03056, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Vas'kevich  |D R.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Vovk  |D M.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/2(2015-02-01), 226-230  |x 1070-4280  |q 51:2<226  |1 2015  |2 51  |o 11178