Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles

Keith C. Coffman, Vy Duong, Alex L. Bagdasarian, James C. Fettinger, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn<sup>0</sup> or Fe<sup>0</sup> dust and HOAc using a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

Original languageEnglish (US)
Pages (from-to)7651-7657
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number34
DOIs
StatePublished - Dec 1 2014

Fingerprint

Isoxazoles
quinoline
Amines
amines
dust
routes
Functional groups
Dust

Keywords

  • Cycloaddition
  • Diversity-oriented synthesis
  • Fused-ring systems
  • Nitrogen heterocycles
  • Oxygen heterocycles
  • Reduction

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Coffman, K. C., Duong, V., Bagdasarian, A. L., Fettinger, J. C., Haddadin, M. J., & Kurth, M. J. (2014). Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles. European Journal of Organic Chemistry, 2014(34), 7651-7657. https://doi.org/10.1002/ejoc.201403065

Heterocycle-to-heterocycle route to quinoline-4-amines : Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles. / Coffman, Keith C.; Duong, Vy; Bagdasarian, Alex L.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.

In: European Journal of Organic Chemistry, Vol. 2014, No. 34, 01.12.2014, p. 7651-7657.

Research output: Contribution to journalArticle

Coffman, KC, Duong, V, Bagdasarian, AL, Fettinger, JC, Haddadin, MJ & Kurth, MJ 2014, 'Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles', European Journal of Organic Chemistry, vol. 2014, no. 34, pp. 7651-7657. https://doi.org/10.1002/ejoc.201403065
Coffman, Keith C. ; Duong, Vy ; Bagdasarian, Alex L. ; Fettinger, James C. ; Haddadin, Makhluf J. ; Kurth, Mark J. / Heterocycle-to-heterocycle route to quinoline-4-amines : Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles. In: European Journal of Organic Chemistry. 2014 ; Vol. 2014, No. 34. pp. 7651-7657.
@article{1d1536d107d04401bb17ab72553a6031,
title = "Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles",
abstract = "A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 dust and HOAc using a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.",
keywords = "Cycloaddition, Diversity-oriented synthesis, Fused-ring systems, Nitrogen heterocycles, Oxygen heterocycles, Reduction",
author = "Coffman, {Keith C.} and Vy Duong and Bagdasarian, {Alex L.} and Fettinger, {James C.} and Haddadin, {Makhluf J.} and Kurth, {Mark J.}",
year = "2014",
month = "12",
day = "1",
doi = "10.1002/ejoc.201403065",
language = "English (US)",
volume = "2014",
pages = "7651--7657",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "34",

}

TY - JOUR

T1 - Heterocycle-to-heterocycle route to quinoline-4-amines

T2 - Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles

AU - Coffman, Keith C.

AU - Duong, Vy

AU - Bagdasarian, Alex L.

AU - Fettinger, James C.

AU - Haddadin, Makhluf J.

AU - Kurth, Mark J.

PY - 2014/12/1

Y1 - 2014/12/1

N2 - A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 dust and HOAc using a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

AB - A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 dust and HOAc using a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

KW - Cycloaddition

KW - Diversity-oriented synthesis

KW - Fused-ring systems

KW - Nitrogen heterocycles

KW - Oxygen heterocycles

KW - Reduction

UR - http://www.scopus.com/inward/record.url?scp=84927144552&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84927144552&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201403065

DO - 10.1002/ejoc.201403065

M3 - Article

AN - SCOPUS:84927144552

VL - 2014

SP - 7651

EP - 7657

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 34

ER -