Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines

Babita Tanwar; Dinesh Kumar; Asim Kumar; Md. Imam Ansari; Mohammad Mohsin Qadri; Maulikkumar D. Vaja; Madhulika Singh; Asit K. Chakraborti

doi:10.1039/c5nj02010g

Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines

Babita Tanwar, Dinesh Kumar, Asim Kumar, Md. Imam Ansari, Mohammad Mohsin Qadri, Maulikkumar D. Vaja, Madhulika Singh, Asit K. Chakraborti^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

The scope and limitations of metal salt Lewis acid catalysts were examined for the selectivity control for the formation of Friedländer and non-Friedländer products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)₃ emerged as the most effective catalyst for the selective/exclusive formation of the Friedländer product. The generality of the In(OTf)₃-catalysed Friedländer reaction was demonstrated by the reaction of differently substituted 2-aminoarylketones with various carbonyl compounds containing an active methylene group (e.g., β-ketoesters, cyclic/acyclic β-diketones, cyclic/acylic ketones, and aryl/heteroaryl methyl ketones) under solvent-free conditions affording the desired quinolines in 75-92% yields.

Original language	English
Pages (from-to)	9824-9833
Number of pages	10
Journal	New Journal of Chemistry
Volume	39
Issue number	12
DOIs	https://doi.org/10.1039/c5nj02010g
Publication status	Published - 13 Oct 2015
Externally published	Yes

Access to Document

10.1039/c5nj02010g

Cite this

@article{41eeb591a6814176aed057a5844bf2fe,

title = "Friedl{\"a}nder annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines",

abstract = "The scope and limitations of metal salt Lewis acid catalysts were examined for the selectivity control for the formation of Friedl{\"a}nder and non-Friedl{\"a}nder products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)3 emerged as the most effective catalyst for the selective/exclusive formation of the Friedl{\"a}nder product. The generality of the In(OTf)3-catalysed Friedl{\"a}nder reaction was demonstrated by the reaction of differently substituted 2-aminoarylketones with various carbonyl compounds containing an active methylene group (e.g., β-ketoesters, cyclic/acyclic β-diketones, cyclic/acylic ketones, and aryl/heteroaryl methyl ketones) under solvent-free conditions affording the desired quinolines in 75-92% yields.",

author = "Babita Tanwar and Dinesh Kumar and Asim Kumar and Ansari, {Md. Imam} and Qadri, {Mohammad Mohsin} and Vaja, {Maulikkumar D.} and Madhulika Singh and Chakraborti, {Asit K.}",

year = "2015",

month = oct,

day = "13",

doi = "10.1039/c5nj02010g",

language = "English",

volume = "39",

pages = "9824--9833",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "12",

}

TY - JOUR

T1 - Friedländer annulation

T2 - scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines

AU - Tanwar, Babita

AU - Kumar, Dinesh

AU - Kumar, Asim

AU - Ansari, Md. Imam

AU - Qadri, Mohammad Mohsin

AU - Vaja, Maulikkumar D.

AU - Singh, Madhulika

AU - Chakraborti, Asit K.

PY - 2015/10/13

Y1 - 2015/10/13

N2 - The scope and limitations of metal salt Lewis acid catalysts were examined for the selectivity control for the formation of Friedländer and non-Friedländer products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)3 emerged as the most effective catalyst for the selective/exclusive formation of the Friedländer product. The generality of the In(OTf)3-catalysed Friedländer reaction was demonstrated by the reaction of differently substituted 2-aminoarylketones with various carbonyl compounds containing an active methylene group (e.g., β-ketoesters, cyclic/acyclic β-diketones, cyclic/acylic ketones, and aryl/heteroaryl methyl ketones) under solvent-free conditions affording the desired quinolines in 75-92% yields.

AB - The scope and limitations of metal salt Lewis acid catalysts were examined for the selectivity control for the formation of Friedländer and non-Friedländer products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)3 emerged as the most effective catalyst for the selective/exclusive formation of the Friedländer product. The generality of the In(OTf)3-catalysed Friedländer reaction was demonstrated by the reaction of differently substituted 2-aminoarylketones with various carbonyl compounds containing an active methylene group (e.g., β-ketoesters, cyclic/acyclic β-diketones, cyclic/acylic ketones, and aryl/heteroaryl methyl ketones) under solvent-free conditions affording the desired quinolines in 75-92% yields.

UR - http://www.scopus.com/inward/record.url?scp=84947976696&partnerID=8YFLogxK

U2 - 10.1039/c5nj02010g

DO - 10.1039/c5nj02010g

M3 - Article

AN - SCOPUS:84947976696

SN - 1144-0546

VL - 39

SP - 9824

EP - 9833

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 12

ER -

Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines

Abstract

Access to Document

Other files and links

Fingerprint

Cite this