Ytterbium-catalyzed synthesis of dihydropyridines

Shunsuke Sueki, Ryo Takei, Junya Abe, Isao Shimizu

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The reaction of anilines, benzaldehydes, and ethyl 3,3-diethoxypropionate in the presence of Yb(OTf)3 proceeded under mild reaction conditions to give dihydropyridines (DHPs). We have found that the reaction depended on the solvent and the DHPs were obtained selectively in 1,4-dioxane as a solvent. Various 2,6-unsubstituted DHPs were synthesized in one pot in satisfactory yields.

Original languageEnglish
Pages (from-to)4473-4477
Number of pages5
JournalTetrahedron Letters
Volume52
Issue number34
DOIs
Publication statusPublished - 2011 Aug 24

Fingerprint

Ytterbium
Dihydropyridines
Aniline Compounds
Benzaldehydes

Keywords

  • 2,6-Unsubstituted dihydropyridine
  • DHP
  • Multi-component coupling reaction
  • Ytterbium catalyst

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Sueki, S., Takei, R., Abe, J., & Shimizu, I. (2011). Ytterbium-catalyzed synthesis of dihydropyridines. Tetrahedron Letters, 52(34), 4473-4477. https://doi.org/10.1016/j.tetlet.2011.06.070

Ytterbium-catalyzed synthesis of dihydropyridines. / Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao.

In: Tetrahedron Letters, Vol. 52, No. 34, 24.08.2011, p. 4473-4477.

Research output: Contribution to journalArticle

Sueki, S, Takei, R, Abe, J & Shimizu, I 2011, 'Ytterbium-catalyzed synthesis of dihydropyridines', Tetrahedron Letters, vol. 52, no. 34, pp. 4473-4477. https://doi.org/10.1016/j.tetlet.2011.06.070
Sueki, Shunsuke ; Takei, Ryo ; Abe, Junya ; Shimizu, Isao. / Ytterbium-catalyzed synthesis of dihydropyridines. In: Tetrahedron Letters. 2011 ; Vol. 52, No. 34. pp. 4473-4477.
@article{6f8124d344ce4fc8af097c6ebbcebf8b,
title = "Ytterbium-catalyzed synthesis of dihydropyridines",
abstract = "The reaction of anilines, benzaldehydes, and ethyl 3,3-diethoxypropionate in the presence of Yb(OTf)3 proceeded under mild reaction conditions to give dihydropyridines (DHPs). We have found that the reaction depended on the solvent and the DHPs were obtained selectively in 1,4-dioxane as a solvent. Various 2,6-unsubstituted DHPs were synthesized in one pot in satisfactory yields.",
keywords = "2,6-Unsubstituted dihydropyridine, DHP, Multi-component coupling reaction, Ytterbium catalyst",
author = "Shunsuke Sueki and Ryo Takei and Junya Abe and Isao Shimizu",
year = "2011",
month = "8",
day = "24",
doi = "10.1016/j.tetlet.2011.06.070",
language = "English",
volume = "52",
pages = "4473--4477",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "34",

}

TY - JOUR

T1 - Ytterbium-catalyzed synthesis of dihydropyridines

AU - Sueki, Shunsuke

AU - Takei, Ryo

AU - Abe, Junya

AU - Shimizu, Isao

PY - 2011/8/24

Y1 - 2011/8/24

N2 - The reaction of anilines, benzaldehydes, and ethyl 3,3-diethoxypropionate in the presence of Yb(OTf)3 proceeded under mild reaction conditions to give dihydropyridines (DHPs). We have found that the reaction depended on the solvent and the DHPs were obtained selectively in 1,4-dioxane as a solvent. Various 2,6-unsubstituted DHPs were synthesized in one pot in satisfactory yields.

AB - The reaction of anilines, benzaldehydes, and ethyl 3,3-diethoxypropionate in the presence of Yb(OTf)3 proceeded under mild reaction conditions to give dihydropyridines (DHPs). We have found that the reaction depended on the solvent and the DHPs were obtained selectively in 1,4-dioxane as a solvent. Various 2,6-unsubstituted DHPs were synthesized in one pot in satisfactory yields.

KW - 2,6-Unsubstituted dihydropyridine

KW - DHP

KW - Multi-component coupling reaction

KW - Ytterbium catalyst

UR - http://www.scopus.com/inward/record.url?scp=79960848799&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79960848799&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.06.070

DO - 10.1016/j.tetlet.2011.06.070

M3 - Article

AN - SCOPUS:79960848799

VL - 52

SP - 4473

EP - 4477

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 34

ER -