In/Cu Catalyzed Multiple C−N/C−C Bond Formation via Multiple Bond Cleavage in a Three Component Synthesis of Arylimidazopyridine Carboxylates

Irwan Iskandar Roslan; Kian Hong Ng; Khalid R. Alhooshani; Stephan Jaenicke; Gaik Khuan Chuah

doi:10.1002/ajoc.202000637

In/Cu Catalyzed Multiple C−N/C−C Bond Formation via Multiple Bond Cleavage in a Three Component Synthesis of Arylimidazopyridine Carboxylates

Irwan Iskandar Roslan
, Kian Hong Ng
, Khalid R. Alhooshani
, Stephan Jaenicke
, Gaik Khuan Chuah^*

^*Corresponding author for this work

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

6 Scopus citations

Abstract

A protocol for In^III and Cu^I co-catalyzed synthesis of a wide array of arylimidazopyridine carboxylates by three components coupling of benzaldehydes, malonic esters and 2-aminopyridines is described. The reaction proceeds through a reaction cascade of Knoevenagel condensation, 1,4-conjugate addition, aerobic dehydrogenation, Ortoleva-King reaction and decarboxylation. Multiple C−N and C−C bond formations in addition to multiple C−C, C−H, C−O, and N−H bond cleavages are involved in forming the product.

Original language	English
Pages (from-to)	554-558
Number of pages	5
Journal	Asian Journal of Organic Chemistry
Volume	10
Issue number	3
DOIs	https://doi.org/10.1002/ajoc.202000637
State	Published - Mar 2021

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Keywords

copper
cyclization
heterocycles
indium
multicomponent reactions

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.202000637

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@article{b064b08bb51e4caabc0bc6c2c8039fb1,

title = "In/Cu Catalyzed Multiple C−N/C−C Bond Formation via Multiple Bond Cleavage in a Three Component Synthesis of Arylimidazopyridine Carboxylates",

abstract = "A protocol for InIII and CuI co-catalyzed synthesis of a wide array of arylimidazopyridine carboxylates by three components coupling of benzaldehydes, malonic esters and 2-aminopyridines is described. The reaction proceeds through a reaction cascade of Knoevenagel condensation, 1,4-conjugate addition, aerobic dehydrogenation, Ortoleva-King reaction and decarboxylation. Multiple C−N and C−C bond formations in addition to multiple C−C, C−H, C−O, and N−H bond cleavages are involved in forming the product.",

keywords = "copper, cyclization, heterocycles, indium, multicomponent reactions",

author = "Roslan, \{Irwan Iskandar\} and Ng, \{Kian Hong\} and Alhooshani, \{Khalid R.\} and Stephan Jaenicke and Chuah, \{Gaik Khuan\}",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",

year = "2021",

month = mar,

doi = "10.1002/ajoc.202000637",

language = "English",

volume = "10",

pages = "554--558",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "John Wiley and Sons Inc.",

number = "3",

}

TY - JOUR

T1 - In/Cu Catalyzed Multiple C−N/C−C Bond Formation via Multiple Bond Cleavage in a Three Component Synthesis of Arylimidazopyridine Carboxylates

AU - Roslan, Irwan Iskandar

AU - Ng, Kian Hong

AU - Alhooshani, Khalid R.

AU - Jaenicke, Stephan

AU - Chuah, Gaik Khuan

PY - 2021/3

Y1 - 2021/3

N2 - A protocol for InIII and CuI co-catalyzed synthesis of a wide array of arylimidazopyridine carboxylates by three components coupling of benzaldehydes, malonic esters and 2-aminopyridines is described. The reaction proceeds through a reaction cascade of Knoevenagel condensation, 1,4-conjugate addition, aerobic dehydrogenation, Ortoleva-King reaction and decarboxylation. Multiple C−N and C−C bond formations in addition to multiple C−C, C−H, C−O, and N−H bond cleavages are involved in forming the product.

AB - A protocol for InIII and CuI co-catalyzed synthesis of a wide array of arylimidazopyridine carboxylates by three components coupling of benzaldehydes, malonic esters and 2-aminopyridines is described. The reaction proceeds through a reaction cascade of Knoevenagel condensation, 1,4-conjugate addition, aerobic dehydrogenation, Ortoleva-King reaction and decarboxylation. Multiple C−N and C−C bond formations in addition to multiple C−C, C−H, C−O, and N−H bond cleavages are involved in forming the product.

KW - copper

KW - cyclization

KW - heterocycles

KW - indium

KW - multicomponent reactions

UR - https://www.scopus.com/pages/publications/85101050727

U2 - 10.1002/ajoc.202000637

DO - 10.1002/ajoc.202000637

M3 - Article

AN - SCOPUS:85101050727

SN - 2193-5807

VL - 10

SP - 554

EP - 558

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 3

ER -

In/Cu Catalyzed Multiple C−N/C−C Bond Formation via Multiple Bond Cleavage in a Three Component Synthesis of Arylimidazopyridine Carboxylates

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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