Ionic liquid-supported synthesis of sulfonamides and carboxamides

Manoj Kumar Muthayala; Bhupender S. Chhikara; Keykavous Parang; Anil Kumar

doi:10.1021/co200149m

Ionic liquid-supported synthesis of sulfonamides and carboxamides

Manoj Kumar Muthayala, Bhupender S. Chhikara, Keykavous Parang, Anil Kumar

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

22 Scopus citations

Abstract

An ionic liquid-supported aldehyde was designed and converted to ionic liquid-supported secondary aryl amines through reductive amination. The reaction of ionic liquid-supported aryl amines with sulfonyl chlorides and acid chlorides, respectively, followed by cleavage using trifluoroacetic acid (TFA) afforded sulfonamides and caboxamides. To introduce additional diversity in the synthesis of sulfonamides and caboxamides, ionic liquid-supported iodosubstituted aryl amine was synthesized using the same strategy, and underwent Suzuki coupling reaction, followed by reaction with a methanesulfonyl chloride to generate the corresponding biaryl sulfonamide. The advantages of the protocol over solid-phase synthesis are homogeneous reaction medium, high loading, easy separation of products, and characterization of intermediates.

Original language	English (US)
Pages (from-to)	60-65
Number of pages	6
Journal	ACS Combinatorial Science
Volume	14
Issue number	1
DOIs	https://doi.org/10.1021/co200149m
State	Published - Jan 9 2012
Externally published	Yes

Keywords

Carboxamides
ionic liquids
parallel synthesis
sulfonamides
Suzuki coupling reaction

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1021/co200149m

Cite this

@article{12576e6485a740eaaf955c4cdae963b7,

title = "Ionic liquid-supported synthesis of sulfonamides and carboxamides",

abstract = "An ionic liquid-supported aldehyde was designed and converted to ionic liquid-supported secondary aryl amines through reductive amination. The reaction of ionic liquid-supported aryl amines with sulfonyl chlorides and acid chlorides, respectively, followed by cleavage using trifluoroacetic acid (TFA) afforded sulfonamides and caboxamides. To introduce additional diversity in the synthesis of sulfonamides and caboxamides, ionic liquid-supported iodosubstituted aryl amine was synthesized using the same strategy, and underwent Suzuki coupling reaction, followed by reaction with a methanesulfonyl chloride to generate the corresponding biaryl sulfonamide. The advantages of the protocol over solid-phase synthesis are homogeneous reaction medium, high loading, easy separation of products, and characterization of intermediates.",

keywords = "Carboxamides, ionic liquids, parallel synthesis, sulfonamides, Suzuki coupling reaction",

author = "Muthayala, {Manoj Kumar} and Chhikara, {Bhupender S.} and Keykavous Parang and Anil Kumar",

year = "2012",

month = jan,

day = "9",

doi = "10.1021/co200149m",

language = "English (US)",

volume = "14",

pages = "60--65",

journal = "Journal of Combinatorial Chemistry",

issn = "2156-8952",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Ionic liquid-supported synthesis of sulfonamides and carboxamides

AU - Muthayala, Manoj Kumar

AU - Chhikara, Bhupender S.

AU - Parang, Keykavous

AU - Kumar, Anil

PY - 2012/1/9

Y1 - 2012/1/9

N2 - An ionic liquid-supported aldehyde was designed and converted to ionic liquid-supported secondary aryl amines through reductive amination. The reaction of ionic liquid-supported aryl amines with sulfonyl chlorides and acid chlorides, respectively, followed by cleavage using trifluoroacetic acid (TFA) afforded sulfonamides and caboxamides. To introduce additional diversity in the synthesis of sulfonamides and caboxamides, ionic liquid-supported iodosubstituted aryl amine was synthesized using the same strategy, and underwent Suzuki coupling reaction, followed by reaction with a methanesulfonyl chloride to generate the corresponding biaryl sulfonamide. The advantages of the protocol over solid-phase synthesis are homogeneous reaction medium, high loading, easy separation of products, and characterization of intermediates.

AB - An ionic liquid-supported aldehyde was designed and converted to ionic liquid-supported secondary aryl amines through reductive amination. The reaction of ionic liquid-supported aryl amines with sulfonyl chlorides and acid chlorides, respectively, followed by cleavage using trifluoroacetic acid (TFA) afforded sulfonamides and caboxamides. To introduce additional diversity in the synthesis of sulfonamides and caboxamides, ionic liquid-supported iodosubstituted aryl amine was synthesized using the same strategy, and underwent Suzuki coupling reaction, followed by reaction with a methanesulfonyl chloride to generate the corresponding biaryl sulfonamide. The advantages of the protocol over solid-phase synthesis are homogeneous reaction medium, high loading, easy separation of products, and characterization of intermediates.

KW - Carboxamides

KW - ionic liquids

KW - parallel synthesis

KW - sulfonamides

KW - Suzuki coupling reaction

UR - http://www.scopus.com/inward/record.url?scp=84862965323&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862965323&partnerID=8YFLogxK

U2 - 10.1021/co200149m

DO - 10.1021/co200149m

M3 - Article

C2 - 22013985

AN - SCOPUS:84862965323

SN - 2156-8952

VL - 14

SP - 60

EP - 65

JO - Journal of Combinatorial Chemistry

JF - Journal of Combinatorial Chemistry

IS - 1

ER -

Ionic liquid-supported synthesis of sulfonamides and carboxamides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this