A highly efficient synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine via a double Suzuki reaction and a Chichibabin cyclization

Michael Palucki; David L. Hughes; Nobuyoshi Yasuda; Chunhua Yang; Paul J. Reider

doi:10.1016/S0040-4039(01)01424-1

A highly efficient synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine via a double Suzuki reaction and a Chichibabin cyclization

Michael Palucki, David L. Hughes, Nobuyoshi Yasuda, Chunhua Yang, Paul J. Reider

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

26 Scopus citations

Abstract

Synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine was accomplished via a one-pot double Suzuki reaction followed by deprotection and a highly regioselective intramolecular Chichibabin cyclization. A variety of reactions conditions were screened for the Chichibabin cyclization including choice of base, solvent and reaction temperature.

Original language	English (US)
Pages (from-to)	6811-6814
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4039(01)01424-1
State	Published - Sep 24 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Amination
Cyclization
Naphthyridines
Suzuki-Miyaura reactions

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10.1016/S0040-4039(01)01424-1

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title = "A highly efficient synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine via a double Suzuki reaction and a Chichibabin cyclization",

abstract = "Synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine was accomplished via a one-pot double Suzuki reaction followed by deprotection and a highly regioselective intramolecular Chichibabin cyclization. A variety of reactions conditions were screened for the Chichibabin cyclization including choice of base, solvent and reaction temperature.",

keywords = "Amination, Cyclization, Naphthyridines, Suzuki-Miyaura reactions",

author = "Michael Palucki and Hughes, \{David L.\} and Nobuyoshi Yasuda and Chunhua Yang and Reider, \{Paul J.\}",

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doi = "10.1016/S0040-4039(01)01424-1",

language = "English (US)",

volume = "42",

pages = "6811--6814",

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TY - JOUR

T1 - A highly efficient synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine via a double Suzuki reaction and a Chichibabin cyclization

AU - Palucki, Michael

AU - Hughes, David L.

AU - Yasuda, Nobuyoshi

AU - Yang, Chunhua

AU - Reider, Paul J.

PY - 2001/9/24

Y1 - 2001/9/24

N2 - Synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine was accomplished via a one-pot double Suzuki reaction followed by deprotection and a highly regioselective intramolecular Chichibabin cyclization. A variety of reactions conditions were screened for the Chichibabin cyclization including choice of base, solvent and reaction temperature.

AB - Synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine was accomplished via a one-pot double Suzuki reaction followed by deprotection and a highly regioselective intramolecular Chichibabin cyclization. A variety of reactions conditions were screened for the Chichibabin cyclization including choice of base, solvent and reaction temperature.

KW - Amination

KW - Cyclization

KW - Naphthyridines

KW - Suzuki-Miyaura reactions

UR - https://www.scopus.com/pages/publications/0035944201

UR - https://www.scopus.com/inward/citedby.url?scp=0035944201&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)01424-1

DO - 10.1016/S0040-4039(01)01424-1

M3 - Article

AN - SCOPUS:0035944201

SN - 0040-4039

VL - 42

SP - 6811

EP - 6814

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

A highly efficient synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine via a double Suzuki reaction and a Chichibabin cyclization

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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