Preparation of Thioflavones via Thiophosphoryl Chloride Mediated Cyclodehydration and Thionation of 1-(2-Hydroxyphenyl)-3-arylpropane-1,3-diones
A simple and convenient one-pot strategy for the preparation of thioflavones from 1,3-diketones is described. Cyclodehydration of a range of beta-diketones and thionation of the resulting flavones was achieved using thiophosphoryl chloride (PSCl3) which serves as both a catalyst and thionating agent...
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Published in | Synthesis (Stuttgart) no. 1; pp. 30 - 32 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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Thieme Medical Publishers
01.01.2011
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Abstract | A simple and convenient one-pot strategy for the preparation of thioflavones from 1,3-diketones is described. Cyclodehydration of a range of beta-diketones and thionation of the resulting flavones was achieved using thiophosphoryl chloride (PSCl3) which serves as both a catalyst and thionating agent. |
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AbstractList | A simple and convenient one-pot strategy for the preparation of thioflavones from 1,3-diketones is described. Cyclodehydration of a range of beta-diketones and thionation of the resulting flavones was achieved using thiophosphoryl chloride (PSCl3) which serves as both a catalyst and thionating agent. |
Author | Pathak, Uma Pandey, Lokesh Kumar Suryanarayana, Malladi V. S. Vimal, Manorama |
Author_xml | – sequence: 1 givenname: Manorama surname: Vimal fullname: Vimal, Manorama email: sc_drde@rediffmail.com organization: Def Res & Dev Estab, Synthet Chem Div, Gwalior 474002, MP, India – sequence: 2 givenname: Uma surname: Pathak fullname: Pathak, Uma organization: Def Res & Dev Estab, Synthet Chem Div, Gwalior 474002, MP, India – sequence: 3 givenname: Lokesh Kumar surname: Pandey fullname: Pandey, Lokesh Kumar organization: Def Res & Dev Estab, Synthet Chem Div, Gwalior 474002, MP, India – sequence: 4 givenname: Malladi V. S. surname: Suryanarayana fullname: Suryanarayana, Malladi V. S. organization: Def Res & Dev Estab, Synthet Chem Div, Gwalior 474002, MP, India |
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Keywords | flavones 4-THIOFLAVONES thiophosphoryl chloride DERIVATIVES thioflavones beta-diketones |
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References | Schonberg, A (WOS:000201199100137) 1931; 64 BAKER, W (WOS:A1954UB69500049) 1954 MAHAL HS (WOS:000286506800006.13) 1933; 4 RAZDAN, RK (WOS:A1978FD60600010) 1978; 21 Mahal, HS (WOS:000188153900212) 1934 WITCZAK, Z (WOS:A1981NW10400005) 1981; 55 Levai, A (WOS:000083600700005) 1999; 5 Pathak, U (WOS:000269494000019) 2009 Dao, TT (WOS:000230180000003) 2005; 28 BALINT J (WOS:000286506800006.6) 1985 COOMBES, RC (WOS:A1983QB43200002) 1983; 14 BA LT (WOS:000286506800006.2) 2006 Pathak, U (WOS:000254544800052) 2008; 73 ALLAN J (WOS:000286506800006.1) 1924; 20 BAKER, W (WOS:A1952UB67200019) 1952 GEISMAN TA (WOS:000286506800006.11) 1952 Baker, W (WOS:000188153700142) 1933 Mughal, EU (WOS:000233001300017) 2005; 11 DUDLEY, KH (WOS:A19679859400074) 1967; 10 BRIGGS MT (WOS:000286506800006.7) 1982; 9 WAGNER H (WOS:000286506800006.21) 1975 Mughal, EU (WOS:000238698800002) 2006; 14 |
References_xml | – volume: 14 start-page: 4704 year: 2006 ident: WOS:000238698800002 article-title: Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones publication-title: BIOORGANIC & MEDICINAL CHEMISTRY doi: 10.1016/j.bmc.2006.03.031 contributor: fullname: Mughal, EU – volume: 28 start-page: 652 year: 2005 ident: WOS:000230180000003 article-title: Synthesis and iNOS inhibitory activities of thioflavones publication-title: ARCHIVES OF PHARMACAL RESEARCH contributor: fullname: Dao, TT – volume: 9 start-page: 2461 year: 1982 ident: WOS:000286506800006.7 publication-title: J CHEM RES MINIPRINT contributor: fullname: BRIGGS MT – volume: 4 start-page: 214 year: 1933 ident: WOS:000286506800006.13 publication-title: CURR SCI contributor: fullname: MAHAL HS – volume: 73 start-page: 2890 year: 2008 ident: WOS:000254544800052 article-title: Expeditious microwave-assisted thionation with the system PSCl3/H2O/Et3N under solvent-free condition publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo7022069 contributor: fullname: Pathak, U – volume: 21 start-page: 643 year: 1978 ident: WOS:A1978FD60600010 article-title: NEW CLASS OF ANTI-MALARIAL DRUGS - DERIVATIVES OF BENZOTHIOPYRANS publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: RAZDAN, RK – start-page: 1303 year: 1952 ident: WOS:A1952UB67200019 article-title: SOME PROPERTIES OF 4-THIONFLAVONE AND ITS METHIODIDE, AND OF 4-THIONCHROMONES publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: BAKER, W – volume: 55 start-page: 763 year: 1981 ident: WOS:A1981NW10400005 article-title: REACTION OF HYDROXYLAMINE WITH 4'-SUBSTITUTED FLAVONE DERIVATIVES publication-title: POLISH JOURNAL OF CHEMISTRY contributor: fullname: WITCZAK, Z – start-page: 1767 year: 1934 ident: WOS:000188153900212 article-title: Synthetical experiments in the chromone group Part XIV The action of sodamide on l-acyloxy-2-acetonaphthones publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: Mahal, HS – volume: 64 start-page: 2323 year: 1931 ident: WOS:000201199100137 article-title: Dichromalenes and the valence tautomeries of unsaturated systems. publication-title: BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT contributor: fullname: Schonberg, A – start-page: 1381 year: 1933 ident: WOS:000188153700142 article-title: Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: Baker, W – volume: 10 start-page: 985 year: 1967 ident: WOS:A19679859400074 article-title: FLAVONOIDS .V. THIATION OF ISOFLAVONES publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: DUDLEY, KH – start-page: 203 year: 2006 ident: WOS:000286506800006.2 publication-title: CHEM COMMUN contributor: fullname: BA LT – volume: 14 start-page: 139 year: 1983 ident: WOS:A1983QB43200002 article-title: ON THE SYNTHESIS OF 2-METHYLCHROMENE-4-THIONE AND 2-METHYL-1-THIOCHROMONE publication-title: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS contributor: fullname: COOMBES, RC – start-page: 5409 year: 2009 ident: WOS:000269494000019 article-title: Ketoximes to N-substituted thioamides via PSCl3 mediated Beckmann rearrangement publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b911844f contributor: fullname: Pathak, U – volume: 20 start-page: 2192 year: 1924 ident: WOS:000286506800006.1 publication-title: J CHEM SOC contributor: fullname: ALLAN J – volume: 5 start-page: 419 year: 1999 ident: WOS:000083600700005 article-title: An efficient procedure for the preparation of 4-thioflavones by the reaction of flavones with Lawesson's Reagent publication-title: HETEROCYCLIC COMMUNICATIONS contributor: fullname: Levai, A – year: 1952 ident: WOS:000286506800006.11 publication-title: CHEM FLAVONOID COMPO contributor: fullname: GEISMAN TA – volume: 11 start-page: 445 year: 2005 ident: WOS:000233001300017 article-title: A facile and cheap method for the conversion of flavones into 4-thioflavones using phosphorus pentasulfide and sodium hydrogen carbonate publication-title: HETEROCYCLIC COMMUNICATIONS contributor: fullname: Mughal, EU – year: 1975 ident: WOS:000286506800006.21 publication-title: FLAVONOIDS contributor: fullname: WAGNER H – year: 1985 ident: WOS:000286506800006.6 publication-title: ORGANIC SULFUR CHEM contributor: fullname: BALINT J – start-page: 998 year: 1954 ident: WOS:A1954UB69500049 article-title: REACTIONS OF 4-THIONCHROMONES WITH AMINO-COMPOUNDS, AND WITH METHYL IODIDE publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: BAKER, W |
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Snippet | A simple and convenient one-pot strategy for the preparation of thioflavones from 1,3-diketones is described. Cyclodehydration of a range of beta-diketones and... |
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Title | Preparation of Thioflavones via Thiophosphoryl Chloride Mediated Cyclodehydration and Thionation of 1-(2-Hydroxyphenyl)-3-arylpropane-1,3-diones |
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