Journal of Organic Chemistry

, volume 84 , issue 10 , pages 6244-6257

Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward S_N^HAr Reaction

B. A. Trofimov ¹

Pavel A. Volkov ¹

Kseniya O Khrapova ¹

Anton A Telezhkin ¹

Nina I. Ivanova ¹

Alexander I Albanov ¹

Nina K. Gusarova ¹

Alexandra M Belogolova ¹

A.B. Trofimov ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russian Federation |

Publication type: Journal Article

Publication date: 2019-04-19

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.9b00519

Copy DOI

PubMed ID: 30999755

Organic Chemistry

Abstract

Quinolines react with acylacetylenes and secondary phosphine chalcogenides at 20-75 °C to afford N-acylvinyl-2(1)-chalcogenophosphoryldihydroquinolines in good and excellent yields. Unlike the pyridine-derived similar intermediates, which eliminate E-alkenes to give aromatic chalcogenophosphorylpyridines, thereby completing SNHAr reaction, with quinolines, the reaction stops at the formation of the above phosphorylated N-acylvinyl-dihydroquinolines, thus representing a pendant SNHAr process. This reaction opens a one-pot atom-economic single-step access to pharmaceutically targeted phosphorylated functionalized dihydroquinolines and isoquinolines.

Found

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Trofimov B. A. et al. Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward SNHAr Reaction // Journal of Organic Chemistry. 2019. Vol. 84. No. 10. pp. 6244-6257.

GOST all authors (up to 50) Copy

Trofimov B. A., Volkov P. A., Khrapova K. O., Telezhkin A. A., Ivanova N. I., Albanov A. I., Gusarova N. K., Belogolova A. M., Trofimov A. Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward SNHAr Reaction // Journal of Organic Chemistry. 2019. Vol. 84. No. 10. pp. 6244-6257.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.9b00519

UR - https://doi.org/10.1021/acs.joc.9b00519

TI - Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward SNHAr Reaction

T2 - Journal of Organic Chemistry

AU - Trofimov, B. A.

AU - Volkov, Pavel A.

AU - Khrapova, Kseniya O

AU - Telezhkin, Anton A

AU - Ivanova, Nina I.

AU - Albanov, Alexander I

AU - Gusarova, Nina K.

AU - Belogolova, Alexandra M

AU - Trofimov, A.B.

PY - 2019

DA - 2019/04/19

PB - American Chemical Society (ACS)

SP - 6244-6257

IS - 10

VL - 84

PMID - 30999755

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Trofimov,

author = {B. A. Trofimov and Pavel A. Volkov and Kseniya O Khrapova and Anton A Telezhkin and Nina I. Ivanova and Alexander I Albanov and Nina K. Gusarova and Alexandra M Belogolova and A.B. Trofimov},

title = {Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward SNHAr Reaction},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {84},

publisher = {American Chemical Society (ACS)},

month = {apr},

url = {https://doi.org/10.1021/acs.joc.9b00519},

number = {10},

pages = {6244--6257},

doi = {10.1021/acs.joc.9b00519}

}

MLA

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MLA Copy

Trofimov, B. A., et al. “Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward SNHAr Reaction.” Journal of Organic Chemistry, vol. 84, no. 10, Apr. 2019, pp. 6244-6257. https://doi.org/10.1021/acs.joc.9b00519.