Synthesis of fluorescent heterocycles: Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

Guillermo Martinez-Ariza; Bereketab T. Mehari; Ludmila A.G. Pinho; Christopher Foley; Kendall Day; John C Jewett; Christopher Hulme

doi:10.1039/c7ob01239j

Synthesis of fluorescent heterocycles: Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

Guillermo Martinez-Ariza, Bereketab T. Mehari, Ludmila A.G. Pinho, Christopher Foley, Kendall Day, John C Jewett, Christopher Hulme

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

19 Scopus citations

Abstract

A concise one-pot three-component reaction that affords fluorescent indolizines, benzo[d]pyrrolo[2,1-b]thiazoles, and pyrrolo[1,2-a]pyrazines is reported. The methodology involves the formation of a heterocyclic 1-aza-1,3-diene derived from a Knoevenagel condensation between an aldehyde and 2-methyl-ene-cyano aza-heterocycles, followed by [4 + 1] cycloaddition of acetyl cyanide behaving as a non-classical isocyanide replacement.

Original language	English (US)
Pages (from-to)	6076-6079
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	29
DOIs	https://doi.org/10.1039/c7ob01239j
State	Published - 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c7ob01239j

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title = "Synthesis of fluorescent heterocycles: Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide",

abstract = "A concise one-pot three-component reaction that affords fluorescent indolizines, benzo[d]pyrrolo[2,1-b]thiazoles, and pyrrolo[1,2-a]pyrazines is reported. The methodology involves the formation of a heterocyclic 1-aza-1,3-diene derived from a Knoevenagel condensation between an aldehyde and 2-methyl-ene-cyano aza-heterocycles, followed by [4 + 1] cycloaddition of acetyl cyanide behaving as a non-classical isocyanide replacement.",

author = "Guillermo Martinez-Ariza and Mehari, {Bereketab T.} and Pinho, {Ludmila A.G.} and Christopher Foley and Kendall Day and Jewett, {John C} and Christopher Hulme",

note = "Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7ob01239j",

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volume = "15",

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publisher = "Royal Society of Chemistry",

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T1 - Synthesis of fluorescent heterocycles

T2 - Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

AU - Martinez-Ariza, Guillermo

AU - Mehari, Bereketab T.

AU - Pinho, Ludmila A.G.

AU - Foley, Christopher

AU - Day, Kendall

AU - Jewett, John C

AU - Hulme, Christopher

PY - 2017

Y1 - 2017

N2 - A concise one-pot three-component reaction that affords fluorescent indolizines, benzo[d]pyrrolo[2,1-b]thiazoles, and pyrrolo[1,2-a]pyrazines is reported. The methodology involves the formation of a heterocyclic 1-aza-1,3-diene derived from a Knoevenagel condensation between an aldehyde and 2-methyl-ene-cyano aza-heterocycles, followed by [4 + 1] cycloaddition of acetyl cyanide behaving as a non-classical isocyanide replacement.

AB - A concise one-pot three-component reaction that affords fluorescent indolizines, benzo[d]pyrrolo[2,1-b]thiazoles, and pyrrolo[1,2-a]pyrazines is reported. The methodology involves the formation of a heterocyclic 1-aza-1,3-diene derived from a Knoevenagel condensation between an aldehyde and 2-methyl-ene-cyano aza-heterocycles, followed by [4 + 1] cycloaddition of acetyl cyanide behaving as a non-classical isocyanide replacement.

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DO - 10.1039/c7ob01239j

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AN - SCOPUS:85026363202

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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ER -

Synthesis of fluorescent heterocycles: Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

Abstract

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CCDC 1445358: Experimental Crystal Structure Determination

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Synthesis of fluorescent heterocycles: Via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide

Abstract

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CCDC 1445358: Experimental Crystal Structure Determination

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