CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines

被引：20

作者：

Bharate, Jaideep B. ^{[1
,2
]}

Abbat, Sheenu ^{[3
,4
]}

Bharatam, Prasad V. ^{[3
,4
]}

Vishwakarma, Ram A. ^{[1
,2
]}

Bharate, Sandip B. ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Integrat Med, Med Chem Div, Jammu 180001, India

[2] CSIR Indian Inst Integrat Med, AcSIR, Jammu 180001, India

[3] Natl Inst Pharmaceut Educ & Res, Dept Pharmacoinformat, Sas Nagar 160062, Punjab, India

[4] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, Sas Nagar 160062, Punjab, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 28期

关键词：

BIOLOGICAL EVALUATION; MOUSE MODEL; CHEMISTRY;

D O I：

10.1039/c5ob00776c

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

Copper bromide catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes directly led to the formation of 3-formyl-2-phenyl-imidazo[1,2-a]pyridines. The quantum chemical calculations were performed to trace the reaction mechanism and get insights into the possible reaction pathway. 2-Aminopyridines on coupling with cinnamaldehyde generate (E)-3-phenyl-3-(pyridin-2-ylamino)acrylaldehyde IV as a key intermediate, which undergoes C-N bond formation reaction to produce 3-formyl-2-phenyl-imidazo[1,2-a] pyridines.

引用

收藏

页码：7790 / 7794

页数：5

相关论文

共 22 条

[1]

Synthesis of imidazo[1,2-a]pyridines: a decade update [J].

Bagdi, Avik Kumar ;

Santra, Sougata ;

Monir, Kamarul ;

Hajra, Alakananda .

CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575

[2]

Kilogram-Scale Synthesis of the CXCR4 Antagonist GSK812397 [J].

Boggs, Sharon ;

Elitzin, Vassil I. ;

Gudmundsson, Kristjan ;

Martin, Michael T. ;

Sharp, Matthew J. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (04) :781-785

[3]

The role of natural product chemistry in drug discovery [J].

Butler, MS .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :2141-2153

[4]

Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen [J].

Cao, Hua ;

Lei, Sai ;

Li, Naiying ;

Chen, Longbin ;

Liu, Jingyun ;

Cai, Huiyin ;

Qiu, Shuxian ;

Tan, Jingwen .

CHEMICAL COMMUNICATIONS, 2015, 51 (10) :1823-1825

[5]

In Vivo SPECT Imaging of Amyloid-β Deposition with Radioiodinated Imidazo[1,2-a] Pyridine Derivative DRM106 in a Mouse Model of Alzheimer's Disease [J].

Chen, Chun-Jen ;

Bando, Kazunori ;

Ashino, Hiroki ;

Taguchi, Kazumi ;

Shiraishi, Hideaki ;

Shima, Keiji ;

Fujimoto, Osuke ;

Kitamura, Chiemi ;

Matsushima, Satoshi ;

Uchida, Keisuke ;

Nakahara, Yuto ;

Kasahara, Hiroyuki ;

Minamizawa, Takao ;

Jiang, Cheng ;

Zhang, Ming-Rong ;

Ono, Maiko ;

Tokunaga, Masaki ;

Suhara, Tetsuya ;

Higuchi, Makoto ;

Yamada, Kazutaka ;

Ji, Bin .

JOURNAL OF NUCLEAR MEDICINE, 2015, 56 (01) :120-126

[6]

Biological evaluation of the radioiodinated imidazo[1,2-a]pyridine derivative DRK092 for amyloid-β imaging in mouse model of Alzheimer's disease [J].

Chen, Chun-Jen ;

Bando, Kazunori ;

Ashino, Hiroki ;

Taguchi, Kazumi ;

Shiraishi, Hideaki ;

Shima, Keiji ;

Fujimoto, Osuke ;

Kitamura, Chiemi ;

Morimoto, Yasuaki ;

Kasahara, Hiroyuki ;

Minamizawa, Takao ;

Jiang, Cheng ;

Zhang, Ming-Rong ;

Suhara, Tetsuya ;

Higuchi, Makoto ;

Yamada, Kazutaka ;

Ji, Bin .

NEUROSCIENCE LETTERS, 2014, 581 :103-108

[7]

Silver-Catalyzed Cyclization of N-(Prop-2-yn-1-yl) pyridin-2-amines [J].

Chioua, Mourad ;

Soriano, Elena ;

Infantes, Lourdes ;

Luisa Jimeno, M. ;

Marco-Contelles, Jose ;

Samadi, Abdelouahid .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (01) :35-39

[8]

Recent progress in the pharmacology of imidazo[1,2-a]pyridines [J].

Enguehard-Gueiffier, Cecile ;

Gueiffier, Alain .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (09) :888-899

[9]

Fang Q. K., 2009, World Pat., Patent No. [WO2009143156, 2009143156, WO 2009/143156 (A2)]

[10]

Gopalan B., 2006, PCT Int. Patent Appl. Pub., Patent No. [WO2006090244, 2006090244, 2006026703]