Copper-Catalyzed Cascade Acylation/Coupling Cyclization Process for the Synthesis of Polycyclic Fused Imidazo[2,1 -b] [1,3]th iazi n ones

Copper-Catalyzed Cascade Acylation/Coupling Cyclization Process for the Synthesis of Polycyclic Fused Imidazo[2,1 -b] [1,3]th iazi n ones

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摘要 A new and efficient cascade synthesis of polycyclic fused imidazo[2,1-b][1,3]thiazinones has been developed. This protocol includes an intermolecular N-acylation followed by a copper-catalyzed intramolecular C--S coupling reaction. The methodology is applied to a wide range of 2-iodo, 2-bromo, and 2-chloro benzoyl chlorides to yield the polycyclic fused imidazo[2,1-b][ 1,3]thiazinones in good to excellent yields. A new and efficient cascade synthesis of polycyclic fused imidazo[2,1-b][1,3]thiazinones has been developed. This protocol includes an intermolecular N-acylation followed by a copper-catalyzed intramolecular C--S coupling reaction. The methodology is applied to a wide range of 2-iodo, 2-bromo, and 2-chloro benzoyl chlorides to yield the polycyclic fused imidazo[2,1-b][ 1,3]thiazinones in good to excellent yields.

作者王治明于斌张秀芹孙小强包伟良

机构地区 School of Petrochemical Engineering Department of Chemistry High Technology Research Institute of Nanjing University

出处《Chinese Journal of Chemistry》 SCIE CAS CSCD 2011年第12期2775-2780,共6页 中国化学（英文版）

基金 Project supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions, the National Natural Science Foundation of China （Nos. 21072168, 21102009） and Natural Science Foundation of Jiangsu Province （No. B K2011230）.

关键词 fused heterocycles cascade reaction copper（I） catalyst 2-halobenzyl chlorides 2-mercaptoimidazole fused heterocycles, cascade reaction, copper（I） catalyst, 2-halobenzyl chlorides, 2-mercaptoimidazole

分类号 TQ225.52 [化学工程—有机化工] X132 [环境科学与工程—环境科学]

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1Dawood, K. M.; Abdel-Wahab, B. F. Chem. Heterocycl. Compd. 2010, 46, 255.
2Mavrova, A. T.; Vuchev, D.; Anichina, K.; Vassilev, N. Eur. J. Med. Chem. 2010, 45, 5856.
3Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Calonghi, N.; Cappadone, C.; Farruggia, G.; Zini, M.; Stefanelli, C.; Masotti, L.; Radin, N. S.; Shoemaker, R. H. J. Med. Chem. 2008, 51,809.
4Huang, W.; Zhao, P.-L.; Liu, C.-L.; Chen, Q.; Liu, Z.-M.; Yang, G.-F. J. Agric. Food Chem. 2007, 55, 3004.
5Pietrancosta, N.; Moumen, A.; Dono, R.; Lingor, P.; Planchamp, V.; Lamballe, F.; Bahr, M.; Kraus, J.-L.; Maina, F. J. Med. Chem. 2006, 49, 3645.
6Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Garaliene, V.; Welsh, W.; Arora, S.; Farruggia, G.; Masotti, L. J. Med. Chem. 2005, 48, 5604.
7Venkatesan, A. M.; Gu, Y.; Dos Santos, O.; Abe, T. Agarwal, A.; Yang, Y.; Petersen, P. J.; Weiss, W. J.; Man sour, T. S.; Nukaga, M.; Hujer, A. M.; Bonomo, R. A. Knox, J. R. J. Med. Chem. 2004, 47, 6556.
8Carcanague, D.; Shue, Y.-K.; Wuonola, M. A.; Uria-Nickelsen, M.; Joubran, C.; Abedi, J. K.; Jones, J.; Kfihler, T. C. J. Med. Chem. 2002, 45, 4300.
9Zou, R.; Ayres, K. R.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1996, 39, 3477.
10Bhaskar, V. H.; Puli, K.; Sangameswaran, B.; Jayakar, B. lndian J. Heterocycl. Chem. 2006, 15, 299.

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2Wang Jing Peng Xigao Zhang Xiaohui.Fused Zirconia[J].China's Refractories,2011,20(4):39-43.
3王俊江.一曝建立碳化—硝化联合反应可行性分析[J].胜炼科技,1997,19(2):10-13.
4英推出一种塑料介体能有效地处理污水[J].中国水产,1988(11):41-41.
5郑博文.持久性污染物多环芳烃的研究进展[J].工业卫生与职业病,2016,42(5):386-390. 被引量：5
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8合成吡啶类化合物用催化剂再生技术[J].精细化工原料及中间体,2003(1):37-37.
9Fused Alumina Refractory Products for Glass Melting Furnace[J].China's Refractories,2001,10(2):42-45.
10佟玲,周瑞泽,吴淑琪,张玲金,李重九.土壤样品中多环芳烃的GC-MS快速分析方法[J].分析测试学报,2008,27(S1):124-126. 被引量：6

Chinese Journal of Chemistry

2011年第12期

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Copper-Catalyzed Cascade Acylation/Coupling Cyclization Process for the Synthesis of Polycyclic Fused Imidazo[2,1 -b] [1,3]th iazi n ones

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