A New Synthesis of Pyrimido[4,5-b]quinoline-2,4(1H,3H)diones (5-Deazaalloxazines) by Oxidative Cyclization of Aryl-bis (6-amino-1,3-dimethyluracil-5-yl) - methanes with Diethyl Azodicarboxylate

Fumio Yoneda, Fusako Takayama, Akira Koshiro

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Treatment of aryl-bis (6-amino-l,3-dimethyluracil-5-yl) methanes, which were prepared by the condensation of 6-amino-1,3-dimethyluracil with aryl aldehydes, with diethyl azodicarboxylate in the presence of sulfolane led to the formation of the corresponding 1.3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)diones (1,3-dimethyl-5-deazaalloxazines).

Original languageEnglish
Pages (from-to)2507-2510
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume27
Issue number10
DOIs
Publication statusPublished - 1979
Externally publishedYes

Fingerprint

Cyclization
Methane
Aldehydes
Condensation
6-amino-1,3-dimethyl uracil
sulfolane
5-deazaflavin
quinoline

Keywords

  • 5-deazaalloxazine
  • bis(6-amino-l,3-dimethyluracil-5-yl)methane
  • diethyl azodicarboxylate
  • oxidative cyclization
  • pyrimido[4,5-b]quinoline

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

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title = "A New Synthesis of Pyrimido[4,5-b]quinoline-2,4(1H,3H)diones (5-Deazaalloxazines) by Oxidative Cyclization of Aryl-bis (6-amino-1,3-dimethyluracil-5-yl) - methanes with Diethyl Azodicarboxylate",
abstract = "Treatment of aryl-bis (6-amino-l,3-dimethyluracil-5-yl) methanes, which were prepared by the condensation of 6-amino-1,3-dimethyluracil with aryl aldehydes, with diethyl azodicarboxylate in the presence of sulfolane led to the formation of the corresponding 1.3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)diones (1,3-dimethyl-5-deazaalloxazines).",
keywords = "5-deazaalloxazine, bis(6-amino-l,3-dimethyluracil-5-yl)methane, diethyl azodicarboxylate, oxidative cyclization, pyrimido[4,5-b]quinoline",
author = "Fumio Yoneda and Fusako Takayama and Akira Koshiro",
year = "1979",
doi = "10.1248/cpb.27.2507",
language = "English",
volume = "27",
pages = "2507--2510",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
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TY - JOUR

T1 - A New Synthesis of Pyrimido[4,5-b]quinoline-2,4(1H,3H)diones (5-Deazaalloxazines) by Oxidative Cyclization of Aryl-bis (6-amino-1,3-dimethyluracil-5-yl) - methanes with Diethyl Azodicarboxylate

AU - Yoneda, Fumio

AU - Takayama, Fusako

AU - Koshiro, Akira

PY - 1979

Y1 - 1979

N2 - Treatment of aryl-bis (6-amino-l,3-dimethyluracil-5-yl) methanes, which were prepared by the condensation of 6-amino-1,3-dimethyluracil with aryl aldehydes, with diethyl azodicarboxylate in the presence of sulfolane led to the formation of the corresponding 1.3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)diones (1,3-dimethyl-5-deazaalloxazines).

AB - Treatment of aryl-bis (6-amino-l,3-dimethyluracil-5-yl) methanes, which were prepared by the condensation of 6-amino-1,3-dimethyluracil with aryl aldehydes, with diethyl azodicarboxylate in the presence of sulfolane led to the formation of the corresponding 1.3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)diones (1,3-dimethyl-5-deazaalloxazines).

KW - 5-deazaalloxazine

KW - bis(6-amino-l,3-dimethyluracil-5-yl)methane

KW - diethyl azodicarboxylate

KW - oxidative cyclization

KW - pyrimido[4,5-b]quinoline

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U2 - 10.1248/cpb.27.2507

DO - 10.1248/cpb.27.2507

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