Pd(II)-Catalyzed Benzimidazole-Assisted Annulation of 3-(1H-Benzo[d]imidazol-2-yl)-2H-chromen-2-one: Access to Imidazo[1,2-a]chromeno[3,4-c]pyridine

被引：1

作者：

Singla, Dinesh ^{[1
]}

Luxami, Vijay ^{[1
]}

Paul, Kamaldeep ^{[1
]}

机构：

[1] Thapar Inst Engn & Technol, Sch Chem & Biochem, Patiala 147001, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 34期

关键词：

coumarin; C-H functionalization; Lippert Plot; oxidative annulation; palladium; CATALYZED OXIDATIVE ANNULATION; H FUNCTIONALIZATION; BIS-COUMARINS; DERIVATIVES; ALKYLATION;

D O I：

10.1002/ejoc.202300531

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed [4+2] oxidative annulation of coumarin-benzimidazoles with olefins for the synthesis of polycyclic aromatic hydrocarbons have been achieved. This synthetic protocol gives access to a wide range of structurally distinct imidazo[1,2-a]chromeno[3,4-c]pyridines in moderate to good yield with wide functional group tolerance. Further, photophysical properties of annulated scaffolds have been examined, which discloses their interesting solvatochromic emission behaviors.

引用

页数：5

共 50 条

[1] Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
Zeng, Dai
Xing, Ai-Ping
Wei, Jun-Jun
Chu, Yi-Xin
Zhang, Shu-Ling
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2019, 234 (02): : 249 - 251
[2] One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives
Wang, Xiang
Chen, Ping
Zhi, Sanjun
Hu, Huayou
Kan, Yuhe
Zhang, Zaichao
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) : 3299 - 3303
[3] Synthesis of Ruthenium Complex Based on 2,6-Bis(1-(phenyl)-1H-benzo[d] imidazol-2-yl) pyridine and 2-(1-Phenyl-1H-benzo[d]imidazol-2-yl)benzoate and Catalytical Oxidation Property of 1-(1H-Benzo[d]imidazol-2-yl) ethanol to 1-(1H-Benzo[d]imidazol-2-yl) ethanone with H2O2
Liu, Shenggui
Pan, Rongkai
Li, Guobi
Su, Wenyi
Ni, Chunlin
JOURNAL OF CHEMISTRY, 2017, 2017
[4] Parallel solid-phase synthesis of disubstituted 3-(1H-benzo[d]imidazol-2-yl) imidazolidine-2,4-diones and 3-(1H-benzo[d]imidazol-2-yl)-2-thioxoimidazolidin-4-ones
Dadiboyena, Sureshbabu
Nefzi, Adel
TETRAHEDRON LETTERS, 2011, 52 (52) : 7030 - 7033
[5] Synthesis of a ruthenium complex based on 2,6-bis[1-(pyridin-2-yl)-1H-benzo[d]imidazol-2-yl]pyridine and catalytic oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehyde with H2 O2
Liu, Shenggui
Pan, Rongkai
Su, Wenyi
Li, Guobi
Ni, Chunlin
JOURNAL OF CHEMICAL RESEARCH, 2017, (02) : 88 - 92
[6] The crystal structure of 1,2-bis(1H-benzo[d]imidazol-2-yl)ethane-1,2-diol - N-(2-aminophenyl)-3-(1H-benzo[d]imidazol-2-yl)-2,3-dihydroxypropanamide (1/1), C32H30N8O5
Clark, Candyce R.
Hosten, Eric C.
Betz, Richard
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2021, 236 (02): : 325 - 327
[7] CRYSTAL STRUCTURE AND PACKING FEATURES OF 3-(5-METHYL-1H-PYRAZOL-3-YL)-2H-CHROMEN-2-ONE AND 3-(3-METHYL-1H-PYRAZOL-3-YL)-2H-CHROMEN-2-ONE
A. Yu. Kostritskiy
M. V. Dmitriev
V. S. Grinev
O. V. Fedotova
Journal of Structural Chemistry, 2021, 62 : 443 - 451
[8] CRYSTAL STRUCTURE AND PACKING FEATURES OF 3-(5-METHYL-1H-PYRAZOL-3-YL)-2H-CHROMEN-2-ONE AND 3-(3-METHYL-1H-PYRAZOL-3-YL)-2H-CHROMEN-2-ONE
Kostritskiy, A. Yu.
Dmitriev, M. V.
Grinev, V. S.
Fedotova, O. V.
JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 62 (03) : 443 - 451
[9] Facile synthesis of substituted benzo[d]pyrrolo[2ʹ,3ʹ:4,5]pyrrolo[1,2-a]imidazoles by 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and arylglyoxals
Farzaneh Alizadeh-Bami
Hossein Mehrabi
Reza Ranjbar-Karimi
Monatshefte für Chemie - Chemical Monthly, 2022, 153 : 913 - 918
[10] Facile synthesis of substituted benzo[d]pyrrolo[2′,3′:4,5] pyrrolo[1,2-a]imidazoles by 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and arylglyoxals
Alizadeh-Bami, Farzaneh
Mehrabi, Hossein
Ranjbar-Karimi, Reza
MONATSHEFTE FUR CHEMIE, 2022, 153 (10): : 913 - 918

← 1 2 3 4 5 →