A new synthetic route to 6,7-dichloro-5,8-quinoxaline-dione and synthesis of its derivatives

Gyoonhee Han; Kye Jung Shin; Dong Chan Kim; Kyung Ho Yoo; Dong Jin Kim; Sang Woo Park

A new synthetic route to 6,7-dichloro-5,8-quinoxaline-dione and synthesis of its derivatives

Gyoonhee Han, Kye Jung Shin, Dong Chan Kim, Kyung Ho Yoo, Dong Jin Kim, Sang Woo Park

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

Abstract

6,7-Dichloro-5,8-quinoxalinedione (2), an analogue of Dichlone®, was prepared from 4-aminophenol (3) in 27% overall yield in 8 steps via chloroxidation of the sulfuric acid salt of 8-amino-5-quinoxalinol (9) as a key step. And two derivatives, 6-chloro-5-hydroxypyrazino[2,3-a]phenazine (10) and pyrido[1,2-a]imidazo[4,5-g]quinoxaline-6,11-dione (11), were prepared by reaction of 2 with 1,2-phenylenediamine and 2-aminopyridine in 79% and 46% yields, respectively.

Original language	English
Pages (from-to)	2496-2502
Number of pages	7
Journal	Heterocycles
Volume	43
Issue number	11
Publication status	Published - 1996

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

Cite this

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title = "A new synthetic route to 6,7-dichloro-5,8-quinoxaline-dione and synthesis of its derivatives",

abstract = "6,7-Dichloro-5,8-quinoxalinedione (2), an analogue of Dichlone{\textregistered}, was prepared from 4-aminophenol (3) in 27% overall yield in 8 steps via chloroxidation of the sulfuric acid salt of 8-amino-5-quinoxalinol (9) as a key step. And two derivatives, 6-chloro-5-hydroxypyrazino[2,3-a]phenazine (10) and pyrido[1,2-a]imidazo[4,5-g]quinoxaline-6,11-dione (11), were prepared by reaction of 2 with 1,2-phenylenediamine and 2-aminopyridine in 79% and 46% yields, respectively.",

author = "Gyoonhee Han and Shin, {Kye Jung} and Kim, {Dong Chan} and Yoo, {Kyung Ho} and Kim, {Dong Jin} and Park, {Sang Woo}",

year = "1996",

language = "English",

volume = "43",

pages = "2496--2502",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

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TY - JOUR

T1 - A new synthetic route to 6,7-dichloro-5,8-quinoxaline-dione and synthesis of its derivatives

AU - Han, Gyoonhee

AU - Shin, Kye Jung

AU - Kim, Dong Chan

AU - Yoo, Kyung Ho

AU - Kim, Dong Jin

AU - Park, Sang Woo

PY - 1996

Y1 - 1996

N2 - 6,7-Dichloro-5,8-quinoxalinedione (2), an analogue of Dichlone®, was prepared from 4-aminophenol (3) in 27% overall yield in 8 steps via chloroxidation of the sulfuric acid salt of 8-amino-5-quinoxalinol (9) as a key step. And two derivatives, 6-chloro-5-hydroxypyrazino[2,3-a]phenazine (10) and pyrido[1,2-a]imidazo[4,5-g]quinoxaline-6,11-dione (11), were prepared by reaction of 2 with 1,2-phenylenediamine and 2-aminopyridine in 79% and 46% yields, respectively.

AB - 6,7-Dichloro-5,8-quinoxalinedione (2), an analogue of Dichlone®, was prepared from 4-aminophenol (3) in 27% overall yield in 8 steps via chloroxidation of the sulfuric acid salt of 8-amino-5-quinoxalinol (9) as a key step. And two derivatives, 6-chloro-5-hydroxypyrazino[2,3-a]phenazine (10) and pyrido[1,2-a]imidazo[4,5-g]quinoxaline-6,11-dione (11), were prepared by reaction of 2 with 1,2-phenylenediamine and 2-aminopyridine in 79% and 46% yields, respectively.

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ER -

A new synthetic route to 6,7-dichloro-5,8-quinoxaline-dione and synthesis of its derivatives

Abstract

All Science Journal Classification (ASJC) codes

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