Pd/Cu‐Catalyzed Cross‐Coupling of Densely Substituted Propargylamines with Aromatic Acyl Chlorides Followed by the Treatment with a Base: Access to Dihydro‐3H‐Pyrrol‐3‐Ones

Pd/Cu‐catalyzed cross‐coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40–45 °C) provides α‐aryl(hetaryl)aminoacetylenic ketones in a yield of up to 97%. The latter undergo cyclization to 1,2,5‐triaryl(hetaryl)‐1,2‐dihydro‐3H‐pyrrol‐3‐ones in up to 93% yield after the trea...

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Published inAdvanced synthesis & catalysis Vol. 365; no. 1; pp. 53 - 67
Main Authors Volkov, Pavel A., Khrapova, Kseniya O., Telezhkin, Anton A., Bidusenko, Ivan A., Schmidt, Elena Yu, Albanov, Alexander I., Trofimov, Boris A.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 10.01.2023
Wiley Subscription Services, Inc
Subjects
acyl chlorides
aminoacetylenic ketones
Chemistry
Chemistry, Applied
Chemistry, Organic
Chlorides
Cross coupling
cyclization
Ethanol
Ketones
Physical Sciences
propargylamines
pyrrol-3-ones
Science & Technology
pyrrol-3-ones
propargylamines
ALCOHOLS
acyl chlorides
aminoacetylenic ketones
ACID
PYRROLIN-4-ONES
CHEMISTRY
cyclization
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Abstract Pd/Cu‐catalyzed cross‐coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40–45 °C) provides α‐aryl(hetaryl)aminoacetylenic ketones in a yield of up to 97%. The latter undergo cyclization to 1,2,5‐triaryl(hetaryl)‐1,2‐dihydro‐3H‐pyrrol‐3‐ones in up to 93% yield after the treatment with KOH or Et2NH (40–55 °C, aqueous ethanol). The one‐pot synthesis of the pyrrol‐3‐ones (in up to 62% yields) by consecutive treatment of the above propargylamines with acyl chlorides (PdCl2/CuI/Ph3P) and a base (KOH) in aqueous ethanol has been also developed.
AbstractList Pd/Cu‐catalyzed cross‐coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40–45 °C) provides α‐aryl(hetaryl)aminoacetylenic ketones in a yield of up to 97%. The latter undergo cyclization to 1,2,5‐triaryl(hetaryl)‐1,2‐dihydro‐3H‐pyrrol‐3‐ones in up to 93% yield after the treatment with KOH or Et2NH (40–55 °C, aqueous ethanol). The one‐pot synthesis of the pyrrol‐3‐ones (in up to 62% yields) by consecutive treatment of the above propargylamines with acyl chlorides (PdCl2/CuI/Ph3P) and a base (KOH) in aqueous ethanol has been also developed.
Pd/Cu-catalyzed cross-coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40-45 degrees C) provides alpha-aryl(hetaryl)aminoacetylenic ketones in a yield of up to 97%. The latter undergo cyclization to 1,2,5-triaryl(hetaryl)-1,2-dihydro-3H-pyrrol-3-ones in up to 93% yield after the treatment with KOH or Et2NH (40-55 degrees C, aqueous ethanol). The one-pot synthesis of the pyrrol-3-ones (in up to 62% yields) by consecutive treatment of the above propargylamines with acyl chlorides (PdCl2/CuI/Ph3P) and a base (KOH) in aqueous ethanol has been also developed.
Author Bidusenko, Ivan A.
Trofimov, Boris A.
Telezhkin, Anton A.
Schmidt, Elena Yu
Khrapova, Kseniya O.
Volkov, Pavel A.
Albanov, Alexander I.
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Issue 1
Keywords pyrrol-3-ones
propargylamines
ALCOHOLS
acyl chlorides
aminoacetylenic ketones
ACID
PYRROLIN-4-ONES
CHEMISTRY
cyclization
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Snippet Pd/Cu‐catalyzed cross‐coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40–45 °C) provides α‐aryl(hetaryl)aminoacetylenic ketones in...
Pd/Cu-catalyzed cross-coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40-45 degrees C) provides alpha-aryl(hetaryl)aminoacetylenic...
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SubjectTerms acyl chlorides
aminoacetylenic ketones
Chemistry
Chemistry, Applied
Chemistry, Organic
Chlorides
Cross coupling
cyclization
Ethanol
Ketones
Physical Sciences
propargylamines
pyrrol-3-ones
Science & Technology
Title Pd/Cu‐Catalyzed Cross‐Coupling of Densely Substituted Propargylamines with Aromatic Acyl Chlorides Followed by the Treatment with a Base: Access to Dihydro‐3H‐Pyrrol‐3‐Ones
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadsc.202201179
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