A Bronsted Acid Catalyzed Easy Access to Conjugated Diene-Diones from Tertiary Propargyl Alcohols and 1,3-Dicarbonyl Compounds

被引：0
作者：
Kalita, Gitumoni [1 ]
Khatua, Snehadrinarayan [2 ]
Chatterjee, Paresh Nath [1 ,3 ]
机构：
[1] Natl Inst Technol Meghalaya, Dept Chem, Bijni Complex, Shillong 793003, Meghalaya, India
[2] North Eastern Hill Univ, Dept Chem, Ctr Adv Studies, Shillong 793022, Meghalaya, India
[3] Natl Inst Technol Durgapur, Dept Chem, Mahatma Gandhi Ave, Durgapur 713209, W Bengal, India
来源：
SYNLETT | 2023年 / 34卷 / 07期
关键词：
Bronsted acid; catalysis; propargyl alcohols; 1,3-dicarbonyl compounds; conjugated diene-diones; ONE-POT SYNTHESIS; TETRASUBSTITUTED FURANS; SUBSTITUTED FURANS; TANDEM REACTION; DERIVATIVES; ALKYLATION; PYRROLES;
D O I：
10.1055/s-0042-1752339
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple protocol catalyzed by a Bronsted acid, trifluoromethanesulfonic acid (CF3SO3H), to synthesize conjugated diene-diones from easily accessible tertiary propargyl alcohols and 1,3-dicarbonyl compounds is described. Reactions are performed in an air atmosphere by using undried solvents with water being the environmentally benign side product of the process. Preliminary synthetic applications of the conjugated diene-diones in the formation of conjugated dieneones and furans are also reported herein.
引用
收藏
页码：815 / 822
页数：8
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  • [1] Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds
    Arcadi, Antonio
    Alfonsi, Maria
    Chiarini, Marco
    Marinelli, Fabio
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) : 576 - 582
  • [2] Ruthenium/TFA-catalyzed coupling of activated secondary propargylic alcohols with cyclic 1,3-diones:: Furan versus pyran ring formation
    Cadierno, Victorio
    Diez, Josefina
    Gimeno, Jose
    Nebra, Noel
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) : 5852 - 5858
  • [3] A novel propargylation/cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds
    Cadierno, Victorio
    Gimeno, Jose
    Nebra, Noel
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) : 382 - 394
  • [4] Efficient access to conjugated dienones and diene-diones from propargylic alcohols and enolizable ketones:: A tandem isomerization/condensation process catalyzed by the sixteen-electron allyl-ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)] [SbF6]
    Cadierno, Victorio
    Diez, Josefina
    Garcia-Garrido, Sergio E.
    Gimeno, Jose
    Nebra, Noel
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) : 2125 - 2132
  • [5] Alkylation of 1,3-dicarbonyl compounds with benzylic and propargylic alcohols using Ir-Sn bimetallic catalyst: synthesis of fully decorated furans and pyrroles
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    Roy, Sujit
    [J]. TETRAHEDRON, 2011, 67 (25) : 4569 - 4577
  • [6] Synthesis of tetrasubstituted furans via In-catalyzed propargylation of 1,3-dicarbonyl compounds-cyclization tandem process
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    Tan, Ze
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    Shen, Youming
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    [J]. TETRAHEDRON LETTERS, 2008, 49 (26) : 4110 - 4112
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    [J]. TETRAHEDRON, 2009, 65 (36) : 7457 - 7463
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    Wang, Jialiang
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    Zhou, Xigeng
    [J]. TETRAHEDRON, 2007, 63 (47) : 11636 - 11643
  • [9] FeCl3-Catalyzed Propargylation-Cycloisomerization Tandem Reaction: A Facile One-Pot Synthesis of Substituted Furans
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    Zhan, Zhuang-ping
    [J]. SYNLETT, 2008, (19) : 3046 - 3052
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    [J]. SYNLETT, 2021, 32 (03) : 304 - 308
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