DMAP-Catalyzed C-N Bond Formation for Diverse Synthesis of Imidazo[1,2-a]pyrimidine and Pyrimido[1,2-a]benzimidazole Derivatives

被引：10

作者：

Shang, Le-Le ^{[1
]}

Feng, Yun ^{[1
]}

Gao, Xing-Lian ^{[1
]}

Chen, Zi-Ren ^{[1
]}

Xia, Yu ^{[1
]}

Jin, Wei-Wei ^{[1
]}

Liu, Chen-Jiang ^{[1
]}

机构：

[1] Xinjiang Univ, Key Lab Oil & Gas Fine Chem, Minist Educ & Xinjiang Uygur Autonomous Reg, Urumqi Key Lab Green Catalysis & Synth Technol,Sc, Urumqi 830046, Xinjiang, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2020年 / 38卷 / 12期

基金：

中国国家自然科学基金;

关键词：

2-Dimethylaminopyridine; Aldehydes; Nitrogen heterocycles; Pyrimido[1,2-a]benzimidazoles; Imidazo[1,2-a]pyrimidines; ONE-POT SYNTHESIS; METAL-FREE; REGIOSELECTIVE SYNTHESIS; ANTIMICROBIAL ACTIVITY; STEP SYNTHESIS; ALPHA; ENTRY; PYRIMIDINE; ALDEHYDES; EFFICIENT;

D O I：

10.1002/cjoc.202000214

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Summary of main observation and conclusion A DMAP (2-dimethylaminopyridine)-catalyzed condensation reactions for the successful direct construction of pyrimido[1,2-a]benzimidazole or imidazo[1,2-a]pyrimidine has been developed. The method utilizes readily available alpha-bromocinnamaldehydes with 2-aminobenzimidazole or 2-aminoimidazole as starting materials in the presence of 2-DMAP/TBHP. In the process, two C-N bonds were successfully constructed to synthesize target compounds. The current method features wide substrate scope, product diversification, and metal-free conditions.

引用

页码：1595 / 1599

页数：5

共 48 条

[1] Synthesis and Antimicrobial Activity of Some New 5-Arylazothiazole, Pyrazolo[1,5-a] Pyrimidine, [1,2,4]Triazolo[4,3-a]Pyrimidine, and Pyrimido[1,2-a]Benzimidazole Derivatives Containing the Thiazole Moiety
Abdelhamid, Abdou O.
Abdelall, Eman K. A.
Abdel-Riheem, Nadia A.
Ahmed, Sayed A.
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (04) : 709 - 718
[2] Synthesis and evaluation of pyrazolo[3,4-b] pyridines and its structural analogues as TNF-α and IL-6 inhibitors
Bharate, Sandip B.
Mahajan, Tushar R.
Gole, Yogesh R.
Nambiar, Mahesh
Matan, T. T.
Kulkarni-Almeida, Asha
Balachandran, Sarala
Junjappa, H.
Balakrishnan, Arun
Vishwakarma, Ram A.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (15) : 7167 - 7176
[3] The role of natural product chemistry in drug discovery
Butler, MS
[J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12): : 2141 - 2153
[4] Base-Catalyzed Povarov Reaction: An Unusual [1,3] Sigmatropic Rearrangement to Dihydropyrimidobenzimidazoles
Chen, Chih-Hau
Yellol, Gorakh S.
Lin, Po-Tsung
Sun, Chung-Ming
[J]. ORGANIC LETTERS, 2011, 13 (19) : 5120 - 5123
[5] Highly Enantioselective Friedel-Crafts Alkylation/N-Hemiacetalization Cascade Reaction with Indoles
Cheng, Hong-Gang
Lu, Liang-Qiu
Wang, Tao
Yang, Qing-Qing
Liu, Xiao-Peng
Li, Yang
Deng, Qiao-Hui
Chen, Jia-Rong
Xiao, Wen-Jing
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3250 - 3254
[6] El-Shekeil A. G., 2012, EUR J CHEM, V3, P356, DOI 10.5155/eurjchem.3.3.356-358.621
[7] Recent progress in the pharmacology of imidazo[1,2-a]pyridines
Enguehard-Gueiffier, Cecile
Gueiffier, Alain
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (09) : 888 - 899
[8] One-Pot Synthesis of Benzo[4,5]imidazo[1,2-a]quinazoline Derivatives via Facile Transition-Metal-Free Tandem Process
Fang, Shuai
Niu, Xiaoyi
Yang, Bingchuan
Li, Yanqiu
Si, Xiaomeng
Feng, Lei
Ma, Chen
[J]. ACS COMBINATORIAL SCIENCE, 2014, 16 (07) : 328 - 332
[9] Synthesis and Antimicrobial Activity of Some New 1,3,4-Thiadiazole Derivatives
Farghaly, Thoraya A.
Abdallah, Magda A.
Aziz, Mohamed R. Abdel
[J]. MOLECULES, 2012, 17 (12) : 14625 - 14636
[10] Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR Products: A Two-Step MCR-Oxidation Protocol toward Functionalized α-Ketoamides and α-Ketotetrazoles
Foley, Christopher
Shaw, Arthur
Hulme, Christopher
[J]. ORGANIC LETTERS, 2017, 19 (09) : 2238 - 2241

← 1 2 3 4 5 →