Polycyclic N-heterocyclic compounds 74

Rearrangement reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with α, ω-dibromoalkanes and evaluation of product bronchodilator activity

Kensuke Okuda, Masahiko Yoshida, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with 1,2-dibromoethane and 1,3-dibromopropane in the presence of a base afforded 2′,13′-dihydrospiro[cyclopropane-1,6′(5′H)-imidazo[2, 1-a]isoquinolin]-5′-ones and 3′,4′-dihydro-2′H- spiro[cyclopropane-1,7′ (6′H)-pyrimido[2,1-a]isoquinolin]-6′- ones, respectively. Certain of the products showed significant bronchodilator activity.

Original languageEnglish
Pages (from-to)865-871
Number of pages7
JournalSynthetic Communications
Volume42
Issue number6
DOIs
Publication statusPublished - 2012

Fingerprint

Heterocyclic Compounds
Bronchodilator Agents
Ethylene Dibromide
cyclopropane
5-amino-1,2-dihydrofuro(2,3-c)isoquinoline
imidazo(2,1-a)isoquinoline
1,3-dibromopropane

Keywords

  • Bronchodilator activity
  • Furo[2,3-c]isoquinoline
  • Rearrangement
  • Ring cleavage
  • Spiroheterocycle

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

@article{556aee3c23994ff3961322f4981adc58,
title = "Polycyclic N-heterocyclic compounds 74: Rearrangement reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with α, ω-dibromoalkanes and evaluation of product bronchodilator activity",
abstract = "Reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with 1,2-dibromoethane and 1,3-dibromopropane in the presence of a base afforded 2′,13′-dihydrospiro[cyclopropane-1,6′(5′H)-imidazo[2, 1-a]isoquinolin]-5′-ones and 3′,4′-dihydro-2′H- spiro[cyclopropane-1,7′ (6′H)-pyrimido[2,1-a]isoquinolin]-6′- ones, respectively. Certain of the products showed significant bronchodilator activity.",
keywords = "Bronchodilator activity, Furo[2,3-c]isoquinoline, Rearrangement, Ring cleavage, Spiroheterocycle",
author = "Kensuke Okuda and Masahiko Yoshida and Takashi Hirota and Kenji Sasaki",
year = "2012",
doi = "10.1080/00397911.2010.532899",
language = "English",
volume = "42",
pages = "865--871",
journal = "Synthetic Communications",
issn = "0039-7911",
publisher = "Taylor and Francis Ltd.",
number = "6",

}

TY - JOUR

T1 - Polycyclic N-heterocyclic compounds 74

T2 - Rearrangement reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with α, ω-dibromoalkanes and evaluation of product bronchodilator activity

AU - Okuda, Kensuke

AU - Yoshida, Masahiko

AU - Hirota, Takashi

AU - Sasaki, Kenji

PY - 2012

Y1 - 2012

N2 - Reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with 1,2-dibromoethane and 1,3-dibromopropane in the presence of a base afforded 2′,13′-dihydrospiro[cyclopropane-1,6′(5′H)-imidazo[2, 1-a]isoquinolin]-5′-ones and 3′,4′-dihydro-2′H- spiro[cyclopropane-1,7′ (6′H)-pyrimido[2,1-a]isoquinolin]-6′- ones, respectively. Certain of the products showed significant bronchodilator activity.

AB - Reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with 1,2-dibromoethane and 1,3-dibromopropane in the presence of a base afforded 2′,13′-dihydrospiro[cyclopropane-1,6′(5′H)-imidazo[2, 1-a]isoquinolin]-5′-ones and 3′,4′-dihydro-2′H- spiro[cyclopropane-1,7′ (6′H)-pyrimido[2,1-a]isoquinolin]-6′- ones, respectively. Certain of the products showed significant bronchodilator activity.

KW - Bronchodilator activity

KW - Furo[2,3-c]isoquinoline

KW - Rearrangement

KW - Ring cleavage

KW - Spiroheterocycle

UR - http://www.scopus.com/inward/record.url?scp=84055177653&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84055177653&partnerID=8YFLogxK

U2 - 10.1080/00397911.2010.532899

DO - 10.1080/00397911.2010.532899

M3 - Article

VL - 42

SP - 865

EP - 871

JO - Synthetic Communications

JF - Synthetic Communications

SN - 0039-7911

IS - 6

ER -