Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke-Blackburn-Bienaymé [4+1]-cycloaddition-Strecker cascade

Guillermo Martinez-Ariza; Jose Nunez-Rios; Yeon Sun Lee; Christopher Hulme

doi:10.1016/j.tetlet.2014.12.127

Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke-Blackburn-Bienaymé [4+1]-cycloaddition-Strecker cascade

Guillermo Martinez-Ariza, Jose Nunez-Rios, Yeon Sun Lee, Christopher Hulme

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

30 Scopus citations

Abstract

A concise one-pot 3-step cascade reaction to biologically significant imidazo[1,2-a]heterocycles is described. The methodology utilizes acetyl cyanide as a non-classical isocyanide replacement for TMSCN in a microwave-assisted [4+1] cycloaddition (the Groebke-Bienaymé-Blackburn reaction) followed by a Strecker reaction under catalysis free conditions. The methodology proceeds with operational simplicity, short reaction times, and high bond forming efficiency.

Original language	English (US)
Pages (from-to)	1038-1040
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2014.12.127
State	Published - Feb 18 2015

Keywords

Bicyclic heterocycles
Groebke-Blackburn-Bienaymé
Imidazopyridine
Multicomponent reaction
Strecker

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.12.127

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title = "Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke-Blackburn-Bienaym{\'e} [4+1]-cycloaddition-Strecker cascade",

abstract = "A concise one-pot 3-step cascade reaction to biologically significant imidazo[1,2-a]heterocycles is described. The methodology utilizes acetyl cyanide as a non-classical isocyanide replacement for TMSCN in a microwave-assisted [4+1] cycloaddition (the Groebke-Bienaym{\'e}-Blackburn reaction) followed by a Strecker reaction under catalysis free conditions. The methodology proceeds with operational simplicity, short reaction times, and high bond forming efficiency.",

keywords = "Bicyclic heterocycles, Groebke-Blackburn-Bienaym{\'e}, Imidazopyridine, Multicomponent reaction, Strecker",

author = "Guillermo Martinez-Ariza and Jose Nunez-Rios and Lee, {Yeon Sun} and Christopher Hulme",

year = "2015",

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T1 - Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke-Blackburn-Bienaymé [4+1]-cycloaddition-Strecker cascade

AU - Martinez-Ariza, Guillermo

AU - Nunez-Rios, Jose

AU - Lee, Yeon Sun

AU - Hulme, Christopher

PY - 2015/2/18

Y1 - 2015/2/18

N2 - A concise one-pot 3-step cascade reaction to biologically significant imidazo[1,2-a]heterocycles is described. The methodology utilizes acetyl cyanide as a non-classical isocyanide replacement for TMSCN in a microwave-assisted [4+1] cycloaddition (the Groebke-Bienaymé-Blackburn reaction) followed by a Strecker reaction under catalysis free conditions. The methodology proceeds with operational simplicity, short reaction times, and high bond forming efficiency.

AB - A concise one-pot 3-step cascade reaction to biologically significant imidazo[1,2-a]heterocycles is described. The methodology utilizes acetyl cyanide as a non-classical isocyanide replacement for TMSCN in a microwave-assisted [4+1] cycloaddition (the Groebke-Bienaymé-Blackburn reaction) followed by a Strecker reaction under catalysis free conditions. The methodology proceeds with operational simplicity, short reaction times, and high bond forming efficiency.

KW - Bicyclic heterocycles

KW - Groebke-Blackburn-Bienaymé

KW - Imidazopyridine

KW - Multicomponent reaction

KW - Strecker

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SN - 0040-4039

VL - 56

SP - 1038

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Acetyl cyanide as a cyanide source in a tandem catalyst-free modified Groebke-Blackburn-Bienaymé [4+1]-cycloaddition-Strecker cascade

Abstract

Keywords

ASJC Scopus subject areas

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