A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles: generation of poly-substituted pyridines

Sunmi Kim; Jeong Hwa Lee; Seok Hyun Yoon; Ikyon Kim

doi:10.1039/d1ob00788b

A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles: generation of poly-substituted pyridines

Sunmi Kim, Jeong Hwa Lee, Seok Hyun Yoon, Ikyon Kim

Department of Pharmacy

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

6 Citations (Scopus)

Abstract

The reaction of β-ketonitrile andN-substituted pyrrole-2-carboxaldehyde in the presence of piperidinium acetate in CH₃CN permitted regioselective access to 5-acylindolizine-7-carbonitrile through a domino Knoevenagel condensation-intramolecular aldol cyclization sequence. A wide range of new indolizine derivatives with a poly-functionalized pyridine moiety were readily synthesized in an atom-economical fashion, thereby expanding the indolizine chemical space for further applications.

Original language	English
Pages (from-to)	5806-5817
Number of pages	12
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	26
DOIs	https://doi.org/10.1039/d1ob00788b
Publication status	Published - 2021 Jul 14

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2021.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/d1ob00788b

Cite this

@article{98262d4a11844070aebf912e8f7b34f6,

title = "A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles: generation of poly-substituted pyridines",

abstract = "The reaction of β-ketonitrile andN-substituted pyrrole-2-carboxaldehyde in the presence of piperidinium acetate in CH3CN permitted regioselective access to 5-acylindolizine-7-carbonitrile through a domino Knoevenagel condensation-intramolecular aldol cyclization sequence. A wide range of new indolizine derivatives with a poly-functionalized pyridine moiety were readily synthesized in an atom-economical fashion, thereby expanding the indolizine chemical space for further applications.",

author = "Sunmi Kim and Lee, {Jeong Hwa} and Yoon, {Seok Hyun} and Ikyon Kim",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = jul,

day = "14",

doi = "10.1039/d1ob00788b",

language = "English",

volume = "19",

pages = "5806--5817",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "26",

}

TY - JOUR

T1 - A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles

T2 - generation of poly-substituted pyridines

AU - Kim, Sunmi

AU - Lee, Jeong Hwa

AU - Yoon, Seok Hyun

AU - Kim, Ikyon

PY - 2021/7/14

Y1 - 2021/7/14

N2 - The reaction of β-ketonitrile andN-substituted pyrrole-2-carboxaldehyde in the presence of piperidinium acetate in CH3CN permitted regioselective access to 5-acylindolizine-7-carbonitrile through a domino Knoevenagel condensation-intramolecular aldol cyclization sequence. A wide range of new indolizine derivatives with a poly-functionalized pyridine moiety were readily synthesized in an atom-economical fashion, thereby expanding the indolizine chemical space for further applications.

AB - The reaction of β-ketonitrile andN-substituted pyrrole-2-carboxaldehyde in the presence of piperidinium acetate in CH3CN permitted regioselective access to 5-acylindolizine-7-carbonitrile through a domino Knoevenagel condensation-intramolecular aldol cyclization sequence. A wide range of new indolizine derivatives with a poly-functionalized pyridine moiety were readily synthesized in an atom-economical fashion, thereby expanding the indolizine chemical space for further applications.

UR - http://www.scopus.com/inward/record.url?scp=85109297324&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85109297324&partnerID=8YFLogxK

U2 - 10.1039/d1ob00788b

DO - 10.1039/d1ob00788b

M3 - Article

C2 - 34113946

AN - SCOPUS:85109297324

SN - 1477-0520

VL - 19

SP - 5806

EP - 5817

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 26

ER -

A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles: generation of poly-substituted pyridines

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this