Base‐Catalyzed Synthesis of N‐Aryl Thioacetamides from Multicomponent Reaction of Phenylacetylenes, Sulfur and Anilines

In the presence of a base catalyst (20 mol %) such as DBU, DABCO or Na2S ⋅ 3H2O/N‐methylpyrrolidone, phenylacetylenes were found to efficiently undergo sulfurative amination with elemental sulfur and anilines under neat conditions, leading to N‐aryl thioamides with complete atom efficiency. “Rien ne...

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Published inEuropean journal of organic chemistry Vol. 27; no. 10
Main Authors Hang Nguyen, Minh, Sam Nguyen, Hai, Anh Nguyen, Le, Ngoc Nguyen, Bich, Thuong Cao, Hai, Hung Mac, Dinh, Binh Nguyen, Thanh
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 11.03.2024
Wiley Subscription Services, Inc
Subjects
Aniline
Aromatic compounds
atom economy
Chemical synthesis
Chemistry
Chemistry, Organic
elemental sulfur
multicomponent reaction
Physical Sciences
Science & Technology
Sodium sulfide
Sulfur
thioamide
thioketene
thioketene
ONE-POT SYNTHESIS
AMINES ACCESS
atom economy
thioamide
THIOAMIDES
multicomponent reaction
elemental sulfur
EFFICIENT
AMIDES
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Summary:In the presence of a base catalyst (20 mol %) such as DBU, DABCO or Na2S ⋅ 3H2O/N‐methylpyrrolidone, phenylacetylenes were found to efficiently undergo sulfurative amination with elemental sulfur and anilines under neat conditions, leading to N‐aryl thioamides with complete atom efficiency. “Rien ne se perd, rien ne se crée”: N‐aryl arylthioacetamides could be formed via base‐catalyzed three‐component reaction of anilines, phenylacetylenes and elemental sulfur with complete atom efficiency.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202301319