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:3
作者
Singla, Dinesh [1 ]
Luxami, Vijay [1 ]
Paul, Kamaldeep [1 ]
机构
[1] Thapar Inst Engn & Technol, Sch Chem & Biochem, Patiala 147001, India
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.
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页数:5
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共 46 条
[1]   Design, synthesis, anticancer activity and molecular docking studies of new benzimidazole derivatives bearing 1,3,4-oxadiazole moieties as potential thymidylate synthase inhibitors [J].
Almalki, Abdulraheem S. A. ;
Nazreen, Syed ;
Elbehairi, Serag Eldin I. ;
Asad, Mohammad ;
Shati, Ali A. ;
Alfaifi, Mohammad Y. ;
Alhadhrami, Abdulrahman ;
Elhenawy, Ahmed A. ;
Alorabi, Ali Q. ;
Asiri, Abdullah M. ;
Alam, Mohammad Mahboob .
NEW JOURNAL OF CHEMISTRY, 2022, 46 (31) :14967-14978
[2]   DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY [J].
ALMIRANTE, L ;
POLO, L ;
MUGNAINI, A ;
PROVINCIALI, E ;
RUGARLI, P ;
BIANCOTTI, A ;
GAMBA, A ;
MURMANN, W .
JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :305-+
[3]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[4]   Novel coumarin benzimidazole derivatives as antioxidants and safer anti-inflammatory agents [J].
Arora, Radha Krishan ;
Kaur, Navneet ;
Bansal, Yogita ;
Bansal, Gulshan .
ACTA PHARMACEUTICA SINICA B, 2014, 4 (05) :368-375
[5]   Exceedingly Fast, Direct Access to Dihydroisoquinolino[1,2-b]quinazolinones through a Ruthenium(II)-Catalyzed Redox-Neutral C-H Allylation/Hydroamination Cascade [J].
Bairy, Gurupada ;
Das, Suvankar ;
Begam, Rhasina Mamataj ;
Jana, Ranjan .
ORGANIC LETTERS, 2018, 20 (22) :7107-7112
[6]   Aldehyde as a Traceless Directing Group for Regioselective C-H Alkylation Catalyzed by Rhodium(III) in Air [J].
Chen, Si-Qi ;
Li, Xin-Ran ;
Li, Chao-Jun ;
Fan, Juan ;
Liu, Zhong-Wen ;
Shi, Xian-Ying .
ORGANIC LETTERS, 2020, 22 (04) :1259-1264
[7]   Rh(III)-Catalyzed C-H Activation/Cycloisomerization of N-Phenoxyacetamides with Enynones for One-Pot Assembly of Furylated 2-Alkenylphenols [J].
Chen, Weijie ;
Liu, Fu-Xiaomin ;
Bian, Mengyao ;
Li, Liping ;
Zhou, Zhi ;
Yi, Wei .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23) :15557-15566
[8]   Palladium Catalyzed Direct Alkenylation of Dihydropyrrolo[2,1-a]isoquinolines through the Oxidative Heck Reaction [J].
Cui, Hai-Lei ;
Liu, Si-Wei ;
Xiao, Xue .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (35) :5729-5734
[9]   Direct Access to Dihydrobenzoimidazo[2,1-a]isoquinolines through Ruthenium-catalyzed Formal [4+2] Annulation [J].
Dhole, Sandip ;
Sun, Chung-Ming .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) :535-541
[10]   Cobalt-Catalyzed Cycloamination: Synthesis and Photophysical Properties of Polycyclic N-Heterocycles [J].
Dong, Yu ;
Yang, Jian ;
Zhang, Hua ;
Zhan, Xiao-Yu ;
He, Shuai ;
Shi, Zhi-Chuan ;
Zhang, Xiao-Mei ;
Wang, Ji-Yu .
ORGANIC LETTERS, 2020, 22 (13) :5151-5156