Regioselective Synthesis of 1-Cyano-3-arylindolizines: Construction of Pyrroles via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines

Dirgha Raj Joshi; Ikyon Kim

doi:10.1002/adsc.202200590

Regioselective Synthesis of 1-Cyano-3-arylindolizines: Construction of Pyrroles via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines

Dirgha Raj Joshi, Ikyon Kim

Department of Pharmacy

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

Abstract

A modular approach to a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible ones. Homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ has been discovered for the first time as well.

Original language	English
Journal	Advanced Synthesis and Catalysis
DOIs	https://doi.org/10.1002/adsc.202200590
Publication status	Published - 2022 Sept 6

Bibliographical note

Funding Information:
. We thank the National Research Foundation of Korea (NRF‐2018R1A6A1A03023718 and NRF‐2020R1A2C2005961) for generous financial support

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.202200590

Cite this

@article{9593e7dc2ab5462994209459744d0ed7,

title = "Regioselective Synthesis of 1-Cyano-3-arylindolizines: Construction of Pyrroles via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines",

abstract = "A modular approach to a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible ones. Homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ has been discovered for the first time as well.",

author = "Joshi, {Dirgha Raj} and Ikyon Kim",

note = "Funding Information: . We thank the National Research Foundation of Korea (NRF‐2018R1A6A1A03023718 and NRF‐2020R1A2C2005961) for generous financial support Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = sep,

day = "6",

doi = "10.1002/adsc.202200590",

language = "English",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

}

TY - JOUR

T1 - Regioselective Synthesis of 1-Cyano-3-arylindolizines

T2 - Construction of Pyrroles via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines

AU - Joshi, Dirgha Raj

AU - Kim, Ikyon

N1 - Funding Information: . We thank the National Research Foundation of Korea (NRF‐2018R1A6A1A03023718 and NRF‐2020R1A2C2005961) for generous financial support Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/9/6

Y1 - 2022/9/6

N2 - A modular approach to a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible ones. Homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ has been discovered for the first time as well.

AB - A modular approach to a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible ones. Homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ has been discovered for the first time as well.

UR - http://www.scopus.com/inward/record.url?scp=85135462780&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85135462780&partnerID=8YFLogxK

U2 - 10.1002/adsc.202200590

DO - 10.1002/adsc.202200590

M3 - Article

AN - SCOPUS:85135462780

SN - 1615-4150

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

ER -

Regioselective Synthesis of 1-Cyano-3-arylindolizines: Construction of Pyrroles via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this