New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes

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Authors

  • Amr M. Abdelmoniem
  • Muhammed A. Ramadan
  • Said A.S. Ghozlan
  • Holger Butenschön
  • Ismail A. Abdelhamid

Research Organisations

External Research Organisations

  • Cairo University
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Details

Original languageEnglish
Article numbere202300009
Number of pages7
JournalCHEMISTRYOPEN
Volume12
Issue number3
Early online date28 Feb 2023
Publication statusPublished - Mar 2023

Abstract

New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes (H. Butenschön, I. A. Abdelhamid et al.) #OpenAccess. Multicomponent reactions (MCRs) are envisaged as an entry point for the synthesis of heterocyclic compounds with interesting biological activities. An efficient approach to annelated tetra(hexa)azacyclopenta[a]anthracenes, tetraazaindeno[5,4-b]fluorenes, and oxatetraazacyclopenta[m]tetraphene was accomplished using a three-component reaction involving 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one with aromatic aldehydes and the corresponding active 1,3-dicarbonyl compounds (namely, dimedone, 1,3-dimethylbarbituric acid, 1,3-indanedione, and 4-hydroxycoumarine). The reactions were conducted in glacial acetic acid at reflux for 5 h to give the desired products in good yields (62–83 %). The chemical constitutions of all new products were confirmed spectroscopically.

Keywords

    heterocycles, multicomponent reactions, oxatetraaza-cyclopenta[m]tetraphene, polyaza-cyclopenta[a]anthracenes, tetraaza-indeno[5,4-b]fluorenes

ASJC Scopus subject areas

Cite this

New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes. / Abdelmoniem, Amr M.; Ramadan, Muhammed A.; Ghozlan, Said A.S. et al.
In: CHEMISTRYOPEN, Vol. 12, No. 3, e202300009, 03.2023.

Research output: Contribution to journalArticleResearchpeer review

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title = "New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes",
abstract = "New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes (H. Butensch{\"o}n, I. A. Abdelhamid et al.) #OpenAccess. Multicomponent reactions (MCRs) are envisaged as an entry point for the synthesis of heterocyclic compounds with interesting biological activities. An efficient approach to annelated tetra(hexa)azacyclopenta[a]anthracenes, tetraazaindeno[5,4-b]fluorenes, and oxatetraazacyclopenta[m]tetraphene was accomplished using a three-component reaction involving 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one with aromatic aldehydes and the corresponding active 1,3-dicarbonyl compounds (namely, dimedone, 1,3-dimethylbarbituric acid, 1,3-indanedione, and 4-hydroxycoumarine). The reactions were conducted in glacial acetic acid at reflux for 5 h to give the desired products in good yields (62–83 %). The chemical constitutions of all new products were confirmed spectroscopically.",
keywords = "heterocycles, multicomponent reactions, oxatetraaza-cyclopenta[m]tetraphene, polyaza-cyclopenta[a]anthracenes, tetraaza-indeno[5,4-b]fluorenes",
author = "Abdelmoniem, {Amr M.} and Ramadan, {Muhammed A.} and Ghozlan, {Said A.S.} and Holger Butensch{\"o}n and Abdelhamid, {Ismail A.}",
note = "Funding Information: Amr M. Abdelmoniem and Ismail A. Abdelhamid acknowledge the Alexander von Humboldt Foundation for research fellowships. ",
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TY - JOUR

T1 - New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes

AU - Abdelmoniem, Amr M.

AU - Ramadan, Muhammed A.

AU - Ghozlan, Said A.S.

AU - Butenschön, Holger

AU - Abdelhamid, Ismail A.

N1 - Funding Information: Amr M. Abdelmoniem and Ismail A. Abdelhamid acknowledge the Alexander von Humboldt Foundation for research fellowships.

PY - 2023/3

Y1 - 2023/3

N2 - New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes (H. Butenschön, I. A. Abdelhamid et al.) #OpenAccess. Multicomponent reactions (MCRs) are envisaged as an entry point for the synthesis of heterocyclic compounds with interesting biological activities. An efficient approach to annelated tetra(hexa)azacyclopenta[a]anthracenes, tetraazaindeno[5,4-b]fluorenes, and oxatetraazacyclopenta[m]tetraphene was accomplished using a three-component reaction involving 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one with aromatic aldehydes and the corresponding active 1,3-dicarbonyl compounds (namely, dimedone, 1,3-dimethylbarbituric acid, 1,3-indanedione, and 4-hydroxycoumarine). The reactions were conducted in glacial acetic acid at reflux for 5 h to give the desired products in good yields (62–83 %). The chemical constitutions of all new products were confirmed spectroscopically.

AB - New Azacycles by One-Pot Three-Component Hantzsch-Like Synthesis of Tetra(hexa)azacyclopenta[a]anthracenes, Tetraazaindeno[5,4-b]fluorenes, and Oxatetraazacyclopenta[m]tetraphenes (H. Butenschön, I. A. Abdelhamid et al.) #OpenAccess. Multicomponent reactions (MCRs) are envisaged as an entry point for the synthesis of heterocyclic compounds with interesting biological activities. An efficient approach to annelated tetra(hexa)azacyclopenta[a]anthracenes, tetraazaindeno[5,4-b]fluorenes, and oxatetraazacyclopenta[m]tetraphene was accomplished using a three-component reaction involving 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one with aromatic aldehydes and the corresponding active 1,3-dicarbonyl compounds (namely, dimedone, 1,3-dimethylbarbituric acid, 1,3-indanedione, and 4-hydroxycoumarine). The reactions were conducted in glacial acetic acid at reflux for 5 h to give the desired products in good yields (62–83 %). The chemical constitutions of all new products were confirmed spectroscopically.

KW - heterocycles

KW - multicomponent reactions

KW - oxatetraaza-cyclopenta[m]tetraphene

KW - polyaza-cyclopenta[a]anthracenes

KW - tetraaza-indeno[5,4-b]fluorenes

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U2 - 10.1002/open.202300009

DO - 10.1002/open.202300009

M3 - Article

AN - SCOPUS:85150977190

VL - 12

JO - CHEMISTRYOPEN

JF - CHEMISTRYOPEN

SN - 2191-1363

IS - 3

M1 - e202300009

ER -

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