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 inSynthesis (Stuttgart) no. 1; pp. 30 - 32
Main Authors Vimal, Manorama, Pathak, Uma, Pandey, Lokesh Kumar, Suryanarayana, Malladi V. S.
Format Journal Article
LanguageEnglish
Published STUTTGART 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.
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
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10.1021/jo7022069
10.1039/b911844f
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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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Chemistry, Organic
Physical Sciences
Science & Technology
Title Preparation of Thioflavones via Thiophosphoryl Chloride Mediated Cyclodehydration and Thionation of 1-(2-Hydroxyphenyl)-3-arylpropane-1,3-diones
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