A direct synthesis of β-carbolines via a three-step one-pot domino approach with a bifunctional Pd/C/K-10 catalyst

Aditya Kulkarni; Abid Shaikh; Béla Török; Xudong Huang

doi:10.1016/j.tetlet.2009.01.143

A direct synthesis of β-carbolines via a three-step one-pot domino approach with a bifunctional Pd/C/K-10 catalyst

Aditya Kulkarni, Abid Shaikh, Béla Török, Xudong Huang

Biochemistry, Chemistry & Physics

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

64 Scopus citations

Abstract

A rapid, microwave-assisted synthesis of β-carbolines via a successive condensation/cyclization/dehydrogenation approach is described. This methodology involves the coupling of various tryptamines with aromatic aldehydes/glyoxals. The product imine undergoes a Pictet-Spengler cyclization followed by a final dehydrogenation to yield β-carbolines in a three-step domino reaction. The use of the bifunctional catalyst Pd/C/K-10 combined with microwave irradiation enabled the synthesis of β-carbolines in short reaction times and in good to excellent yields.

Original language	English
Pages (from-to)	1791-1794
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2009.01.143
State	Published - Apr 22 2009

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Aromatization
Microwave irradiation
Montmorillonite K-10
Pictet-Spengler cyclization
Solid acid/metal bifunctional catalysis
β-Carbolines

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10.1016/j.tetlet.2009.01.143

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title = "A direct synthesis of β-carbolines via a three-step one-pot domino approach with a bifunctional Pd/C/K-10 catalyst",

abstract = "A rapid, microwave-assisted synthesis of β-carbolines via a successive condensation/cyclization/dehydrogenation approach is described. This methodology involves the coupling of various tryptamines with aromatic aldehydes/glyoxals. The product imine undergoes a Pictet-Spengler cyclization followed by a final dehydrogenation to yield β-carbolines in a three-step domino reaction. The use of the bifunctional catalyst Pd/C/K-10 combined with microwave irradiation enabled the synthesis of β-carbolines in short reaction times and in good to excellent yields.",

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T1 - A direct synthesis of β-carbolines via a three-step one-pot domino approach with a bifunctional Pd/C/K-10 catalyst

AU - Kulkarni, Aditya

AU - Shaikh, Abid

AU - Török, Béla

AU - Huang, Xudong

PY - 2009/4/22

Y1 - 2009/4/22

N2 - A rapid, microwave-assisted synthesis of β-carbolines via a successive condensation/cyclization/dehydrogenation approach is described. This methodology involves the coupling of various tryptamines with aromatic aldehydes/glyoxals. The product imine undergoes a Pictet-Spengler cyclization followed by a final dehydrogenation to yield β-carbolines in a three-step domino reaction. The use of the bifunctional catalyst Pd/C/K-10 combined with microwave irradiation enabled the synthesis of β-carbolines in short reaction times and in good to excellent yields.

AB - A rapid, microwave-assisted synthesis of β-carbolines via a successive condensation/cyclization/dehydrogenation approach is described. This methodology involves the coupling of various tryptamines with aromatic aldehydes/glyoxals. The product imine undergoes a Pictet-Spengler cyclization followed by a final dehydrogenation to yield β-carbolines in a three-step domino reaction. The use of the bifunctional catalyst Pd/C/K-10 combined with microwave irradiation enabled the synthesis of β-carbolines in short reaction times and in good to excellent yields.

KW - Aromatization

KW - Microwave irradiation

KW - Montmorillonite K-10

KW - Pictet-Spengler cyclization

KW - Solid acid/metal bifunctional catalysis

KW - β-Carbolines

UR - https://www.scopus.com/pages/publications/61349168448

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DO - 10.1016/j.tetlet.2009.01.143

M3 - Article

SN - 0040-4039

VL - 50

SP - 1791

EP - 1794

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

A direct synthesis of β-carbolines via a three-step one-pot domino approach with a bifunctional Pd/C/K-10 catalyst

Abstract

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Keywords

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