Symmetrical Trichlorotriazine Derivatives as Efficient Reagents for One-Pot Synthesis of 3-Acetyl-2-chloroquinolines from Acetanilides under Vilsmeier-Haack Conditions

Symmetrical trichlorotriazine derivatives such as 2,4,6-trichloro-1,3,5-triazine and trichloroisocyanuric acid were explored as Vilsmeier-Haack type reagents in the presence of N,N-dimethylacetamide for the effective synthesis of 3-acetyl-2-chloroquinolines from acetanilides. Ultrasonication led to...

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Bibliographic Details
Published inSynlett Vol. 29; no. 1; pp. 85 - 88
Main Authors Muddam, Bhooshan, Venkanna, P., Venkateswarlu, M., Kumar, M. Satish, Rajanna, K. C.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.01.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
MICELLAR MEDIA
ENANTIOSELECTIVITY
acetanilides
AMPHIPHILES
trichlorotriazines
Vilsmeier-Haack reaction
CATALYZED ASYMMETRIC HYDROGENATION
MILD
chloroacetylquinolines
2-CHLORO-3-FORMYL QUINOLINES
sonication
CYANURIC CHLORIDE
BECKMANN REARRANGEMENT
CARBOXYLIC-ACIDS
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Summary:Symmetrical trichlorotriazine derivatives such as 2,4,6-trichloro-1,3,5-triazine and trichloroisocyanuric acid were explored as Vilsmeier-Haack type reagents in the presence of N,N-dimethylacetamide for the effective synthesis of 3-acetyl-2-chloroquinolines from acetanilides. Ultrasonication led to shorter reaction times than conventional heating and gave yields comparable to those obtained under reflux conditions.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1589099