Synthesis of Binuclear Isoquinoline- and Pyridine-Fused Benzimidazole-4,7-diones by Magnetic MOF-199-Catalyzed C–C Coupling/Cyclization Followed by Oxidation

Thi Duyen Diep; Pham Duy Quang Dao; Chan Sik Cho

doi:10.1002/ejoc.201900635

Synthesis of Binuclear Isoquinoline- and Pyridine-Fused Benzimidazole-4,7-diones by Magnetic MOF-199-Catalyzed C–C Coupling/Cyclization Followed by Oxidation

Thi Duyen Diep
, Pham Duy Quang Dao
, Chan Sik Cho

Department of Applied Chemistry

Kyungpook National University

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

20 Scopus citations

Abstract

2-(2-bromoaryl)-4,7-dimethoxy-1H-benzo[d]imidazoles and (Z)-2-(2-bromovinyl)-4,7-dimethoxy-1H-benzo[d]imidazoles react with 1,3-diketones by microwave irradiation in DMF in the presence of a catalytic amount of recyclable Fe₃O₄@SiO₂@MOF-199 along with a base to give binuclear isoquinoline- and pyridine-fused benzimidazoles, respectively. Treatment of such binuclear N-fused hybrid scaffolds with ceric ammonium nitrate in acetonitrile/H₂O or HBr/FeCl₃ in H₂O affords binuclear isoquinoline- and pyridine-fused benzimidazole-4,7-diones in good to high yields.

Original language	English
Pages (from-to)	4071-4079
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201900635
State	Published - 7 Jul 2019

Keywords

Benzimidazole-4,7-dione
Heterocycles
Heterogeneous catalysis
Isoquinoline
Pyridine

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10.1002/ejoc.201900635

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@article{ed08bb1241494ef3bd0f31f32e9ec349,

title = "Synthesis of Binuclear Isoquinoline- and Pyridine-Fused Benzimidazole-4,7-diones by Magnetic MOF-199-Catalyzed C–C Coupling/Cyclization Followed by Oxidation",

abstract = "2-(2-bromoaryl)-4,7-dimethoxy-1H-benzo[d]imidazoles and (Z)-2-(2-bromovinyl)-4,7-dimethoxy-1H-benzo[d]imidazoles react with 1,3-diketones by microwave irradiation in DMF in the presence of a catalytic amount of recyclable Fe3O4@SiO2@MOF-199 along with a base to give binuclear isoquinoline- and pyridine-fused benzimidazoles, respectively. Treatment of such binuclear N-fused hybrid scaffolds with ceric ammonium nitrate in acetonitrile/H2O or HBr/FeCl3 in H2O affords binuclear isoquinoline- and pyridine-fused benzimidazole-4,7-diones in good to high yields.",

keywords = "Benzimidazole-4,7-dione, Heterocycles, Heterogeneous catalysis, Isoquinoline, Pyridine",

author = "Diep, \{Thi Duyen\} and Dao, \{Pham Duy Quang\} and Cho, \{Chan Sik\}",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = jul,

day = "7",

doi = "10.1002/ejoc.201900635",

language = "English",

volume = "2019",

pages = "4071--4079",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "25",

}

Synthesis of Binuclear Isoquinoline- and Pyridine-Fused Benzimidazole-4,7-diones by Magnetic MOF-199-Catalyzed C–C Coupling/Cyclization Followed by Oxidation. / Diep, Thi Duyen; Dao, Pham Duy Quang; Cho, Chan Sik.
In: European Journal of Organic Chemistry, Vol. 2019, No. 25, 07.07.2019, p. 4071-4079.

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

TY - JOUR

T1 - Synthesis of Binuclear Isoquinoline- and Pyridine-Fused Benzimidazole-4,7-diones by Magnetic MOF-199-Catalyzed C–C Coupling/Cyclization Followed by Oxidation

AU - Diep, Thi Duyen

AU - Dao, Pham Duy Quang

AU - Cho, Chan Sik

PY - 2019/7/7

Y1 - 2019/7/7

N2 - 2-(2-bromoaryl)-4,7-dimethoxy-1H-benzo[d]imidazoles and (Z)-2-(2-bromovinyl)-4,7-dimethoxy-1H-benzo[d]imidazoles react with 1,3-diketones by microwave irradiation in DMF in the presence of a catalytic amount of recyclable Fe3O4@SiO2@MOF-199 along with a base to give binuclear isoquinoline- and pyridine-fused benzimidazoles, respectively. Treatment of such binuclear N-fused hybrid scaffolds with ceric ammonium nitrate in acetonitrile/H2O or HBr/FeCl3 in H2O affords binuclear isoquinoline- and pyridine-fused benzimidazole-4,7-diones in good to high yields.

AB - 2-(2-bromoaryl)-4,7-dimethoxy-1H-benzo[d]imidazoles and (Z)-2-(2-bromovinyl)-4,7-dimethoxy-1H-benzo[d]imidazoles react with 1,3-diketones by microwave irradiation in DMF in the presence of a catalytic amount of recyclable Fe3O4@SiO2@MOF-199 along with a base to give binuclear isoquinoline- and pyridine-fused benzimidazoles, respectively. Treatment of such binuclear N-fused hybrid scaffolds with ceric ammonium nitrate in acetonitrile/H2O or HBr/FeCl3 in H2O affords binuclear isoquinoline- and pyridine-fused benzimidazole-4,7-diones in good to high yields.

KW - Benzimidazole-4,7-dione

KW - Heterocycles

KW - Heterogeneous catalysis

KW - Isoquinoline

KW - Pyridine

UR - https://www.scopus.com/pages/publications/85067659755

U2 - 10.1002/ejoc.201900635

DO - 10.1002/ejoc.201900635

M3 - Article

AN - SCOPUS:85067659755

SN - 1434-193X

VL - 2019

SP - 4071

EP - 4079

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

Synthesis of Binuclear Isoquinoline- and Pyridine-Fused Benzimidazole-4,7-diones by Magnetic MOF-199-Catalyzed C–C Coupling/Cyclization Followed by Oxidation

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