A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl) quinolines from morita-baylis-hillman adducts and their oxidation to the corresponding sulfones

Chintakunta Ramesh; Po Min Lei; Veerababurao Kavala; Chun Wei Kuo; Ching Fa Yao

doi:10.3390/molecules17055081

A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl) quinolines from morita-baylis-hillman adducts and their oxidation to the corresponding sulfones

Chintakunta Ramesh, Po Min Lei, Veerababurao Kavala, Chun Wei Kuo, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

5 Citations (Scopus)

Abstract

A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3- (phenylthiomethyl)quinolines were transformed into 2-methyl-3- (phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation

Original language	English
Pages (from-to)	5081-5094
Number of pages	14
Journal	Molecules
Volume	17
Issue number	5
DOIs	https://doi.org/10.3390/molecules17055081
Publication status	Published - 2012 May

Keywords

Fe/AcOH
Morita-Baylis-Hillman adducts
One-pot procedure
Quinolines
Reductive cyclization

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.3390/molecules17055081

Cite this

@article{96db399badc84639a60530aceebb629a,

title = "A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl) quinolines from morita-baylis-hillman adducts and their oxidation to the corresponding sulfones",

abstract = "A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3- (phenylthiomethyl)quinolines were transformed into 2-methyl-3- (phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation",

keywords = "Fe/AcOH, Morita-Baylis-Hillman adducts, One-pot procedure, Quinolines, Reductive cyclization",

author = "Chintakunta Ramesh and Lei, {Po Min} and Veerababurao Kavala and Kuo, {Chun Wei} and Yao, {Ching Fa}",

year = "2012",

month = may,

doi = "10.3390/molecules17055081",

language = "English",

volume = "17",

pages = "5081--5094",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "5",

}

TY - JOUR

T1 - A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl) quinolines from morita-baylis-hillman adducts and their oxidation to the corresponding sulfones

AU - Ramesh, Chintakunta

AU - Lei, Po Min

AU - Kavala, Veerababurao

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

PY - 2012/5

Y1 - 2012/5

N2 - A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3- (phenylthiomethyl)quinolines were transformed into 2-methyl-3- (phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation

AB - A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3- (phenylthiomethyl)quinolines were transformed into 2-methyl-3- (phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation

KW - Fe/AcOH

KW - Morita-Baylis-Hillman adducts

KW - One-pot procedure

KW - Quinolines

KW - Reductive cyclization

UR - http://www.scopus.com/inward/record.url?scp=84861492177&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84861492177&partnerID=8YFLogxK

U2 - 10.3390/molecules17055081

DO - 10.3390/molecules17055081

M3 - Article

C2 - 22555297

AN - SCOPUS:84861492177

SN - 1420-3049

VL - 17

SP - 5081

EP - 5094

JO - Molecules

JF - Molecules

IS - 5

ER -

A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl) quinolines from morita-baylis-hillman adducts and their oxidation to the corresponding sulfones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 836385: Experimental Crystal Structure Determination

Cite this

A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl) quinolines from morita-baylis-hillman adducts and their oxidation to the corresponding sulfones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 836385: Experimental Crystal Structure Determination

Cite this