An Efficient Synthesis of Pyrrolo[1,2-a] or Pyrido[1,2-a]benzo[4,5]imidazo[1,2-c]quinazoline Derivatives in Ionic Liquids Catalyzed by Iodine

被引：5

作者：

Wang, Yue ^{[1
]}

Liu, Jian-Quan ^{[1
]}

Wang, Xiang-Shan ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Jiangsu Key Lab Green Synthet Chem Funct Mat, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2017年 / 54卷 / 06期

关键词：

ONE-POT SYNTHESIS; GREEN SYNTHESIS; ALKALOIDS; INHIBITORS; CASCADE;

D O I：

10.1002/jhet.2967

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(1H-benzo[d]imidazol-2-yl)anilines reacted with haloketones including 5-chloropentan-2-one and 6-chlorohexan-2-one catalyzed by iodine, giving benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazoline and 6H-benzo[4,5]imidazo[1,2-c]pyrido[1,2-a]quinazoline derivatives, respectively. This domino-type reaction formed two new heterocycles and three new covalent bonds in one-pot procedure and provided a green method for the synthesis of fused pentacyclic heterocycles bearing both quinazoline and benzimidazole moieties in ionic liquids.

引用

收藏

页码：3440 / 3446

页数：7

相关论文

共 28 条

[1] Synthesis of benzoimidazoquinazolines by cobalt-catalyzed isocyanide insertion-cyclization [J].

Ahmadi, Fereshteh ;

Bazgir, Ayoob .

RSC ADVANCES, 2016, 6 (66) :61955-61958

[2] Catalyst-Dependent Selectivity in the Relay Catalytic Branching Cascade [J].

Bansode, Avinash H. ;

Shaikh, Aslam C. ;

Kavthe, Rahul D. ;

Thorat, Shridhar ;

Gonnade, Rajesh G. ;

Patil, Nitin T. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (06) :2319-2323

[3] Combined effect of ether and siloxane substituents on imidazolium ionic liquids [J].

Chavan, Santosh N. ;

Mandal, Debaprasad .

RSC ADVANCES, 2015, 5 (80) :64821-64831

[4] New Quinolinone Alkaloids from Chestnut (Castanea crenata Sieb) Honey [J].

Cho, Jeong-Yong ;

Bae, Sun-Hee ;

Kim, Hye-Kyung ;

Lee, Myeong-Lyeol ;

Choi, Yong-Soo ;

Jin, Byung-Rae ;

Lee, Hyoung Jae ;

Jeong, Hang Yeon ;

Lee, Yu Geon ;

Moon, Jae-Hak .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2015, 63 (13) :3587-3592

[5] One-Pot Synthesis of Benzo[4,5]imidazo[1,2-a]quinazoline Derivatives via Facile Transition-Metal-Free Tandem Process [J].

Fang, Shuai ;

Niu, Xiaoyi ;

Yang, Bingchuan ;

Li, Yanqiu ;

Si, Xiaomeng ;

Feng, Lei ;

Ma, Chen .

ACS COMBINATORIAL SCIENCE, 2014, 16 (07) :328-332

[6] Iodine-catalyzed synthesis of dibenzo[b,h][1,6]-naphthyridine-11-carboxamides via a domino reaction involving double elimination of hydrogen bromide [J].

Feng, Bin-Bin ;

Lu, Lian ;

Li, Chao ;

Wang, Xiang-Shan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (09) :2774-2779

[7] New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives [J].

Harutyunyan, A. A. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (07) :1012-1017

[8]

Ito C, 1999, CHEM PHARM BULL, V47, P1491

[9] Au(I)/Ag(I)-Catalyzed Cascade Approach for the Synthesis of Benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinones [J].

Ji, Xun ;

Zhou, Yu ;

Wang, Jinfang ;

Zhao, Linxiang ;

Jiang, Hualiang ;

Liu, Hong .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09) :4312-4318

[10] Iodine-catalyzed synthesis of 5H-phthalazino[1,2-b]quinazoline and isoindolo[2,1-a]quinazoline derivatives via a chemoselective reaction of 2-aminobenzohydrazide and 2-formylbenzoic acid in ionic liquids [J].

Jin, Rong-Zhang ;

Zhang, Wen-Ting ;

Zhou, Yu-Jing ;

Wang, Xiang-Shan .

TETRAHEDRON LETTERS, 2016, 57 (23) :2515-2519