Design and synthesis of α-aminonitrile-functionalized novel retinoids

Bhaskar C. Das; Jaime Anguiano; Sakkarapalayam M. Mahalingam

doi:10.1016/j.tetlet.2009.07.119

Design and synthesis of α-aminonitrile-functionalized novel retinoids

Bhaskar C. Das
, Jaime Anguiano
, Sakkarapalayam M. Mahalingam

Pharmaceutical Sciences

Albert Einstein College of Medicine

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

11 Scopus citations

Abstract

We have developed an expedient one-pot method for the synthesis of α-aminonitrile-functionalized new retinoids via a three-component condensation of β-cyclocitral, amine, and TMSCN (trimethyl silylcyanide) in the presence of a catalytic amount of indium(III) chloride in water. The reactions proceeded smoothly at room temperature in water to generate the corresponding retinoids in moderate to excellent yields (85-92%). In addition, the utility of this reaction was demonstrated to synthesize boron-containing retinoids.

Original language	English
Pages (from-to)	5670-5672
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2009.07.119
State	Published - Oct 7 2009

Keywords

α-Aminonitrile
Boron-containing retinoids
Pinacolatoborane
Retinoids

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10.1016/j.tetlet.2009.07.119

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title = "Design and synthesis of α-aminonitrile-functionalized novel retinoids",

abstract = "We have developed an expedient one-pot method for the synthesis of α-aminonitrile-functionalized new retinoids via a three-component condensation of β-cyclocitral, amine, and TMSCN (trimethyl silylcyanide) in the presence of a catalytic amount of indium(III) chloride in water. The reactions proceeded smoothly at room temperature in water to generate the corresponding retinoids in moderate to excellent yields (85-92\%). In addition, the utility of this reaction was demonstrated to synthesize boron-containing retinoids.",

keywords = "α-Aminonitrile, Boron-containing retinoids, Pinacolatoborane, Retinoids",

author = "Das, \{Bhaskar C.\} and Jaime Anguiano and Mahalingam, \{Sakkarapalayam M.\}",

year = "2009",

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doi = "10.1016/j.tetlet.2009.07.119",

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TY - JOUR

T1 - Design and synthesis of α-aminonitrile-functionalized novel retinoids

AU - Das, Bhaskar C.

AU - Anguiano, Jaime

AU - Mahalingam, Sakkarapalayam M.

PY - 2009/10/7

Y1 - 2009/10/7

N2 - We have developed an expedient one-pot method for the synthesis of α-aminonitrile-functionalized new retinoids via a three-component condensation of β-cyclocitral, amine, and TMSCN (trimethyl silylcyanide) in the presence of a catalytic amount of indium(III) chloride in water. The reactions proceeded smoothly at room temperature in water to generate the corresponding retinoids in moderate to excellent yields (85-92%). In addition, the utility of this reaction was demonstrated to synthesize boron-containing retinoids.

AB - We have developed an expedient one-pot method for the synthesis of α-aminonitrile-functionalized new retinoids via a three-component condensation of β-cyclocitral, amine, and TMSCN (trimethyl silylcyanide) in the presence of a catalytic amount of indium(III) chloride in water. The reactions proceeded smoothly at room temperature in water to generate the corresponding retinoids in moderate to excellent yields (85-92%). In addition, the utility of this reaction was demonstrated to synthesize boron-containing retinoids.

KW - α-Aminonitrile

KW - Boron-containing retinoids

KW - Pinacolatoborane

KW - Retinoids

UR - https://www.scopus.com/pages/publications/68749085966

U2 - 10.1016/j.tetlet.2009.07.119

DO - 10.1016/j.tetlet.2009.07.119

M3 - Article

AN - SCOPUS:68749085966

SN - 0040-4039

VL - 50

SP - 5670

EP - 5672

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

Design and synthesis of α-aminonitrile-functionalized novel retinoids

Abstract

Keywords

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