水合三氯金酸钠(III)催化高效合成 1,5-苯并二氮杂卓和喹喔啉衍生物。
Sodium tetrachloroaurate(III) dihydrate-catalyzed efficient synthesis of 1,5-benzodiazepine and quinoxaline derivatives.
机构信息
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, China.
出版信息
J Zhejiang Univ Sci B. 2010 Feb;11(2):102-8. doi: 10.1631/jzus.B0900288.
Abstract
Both 1,5-benzodiazepine and quinoxaline derivatives are important heterocycles in pharmaceuticals. We describe an efficient and clean method for the synthesis of 1,5-benzodiazepines from o-phenylenediamine and ketones catalyzed by sodium tetrachloroaurate(III) dihydrate under mild conditions. The catalyst was shown to be equally effective for the synthesis of quinoxalines from o-phenylenediamine and alpha-bromo ketones under the similar reaction conditions. This method produced good yields.
摘要
1,5-苯并二氮杂卓和喹喔啉衍生物都是药物中重要的杂环。我们描述了一种在温和条件下，由邻苯二胺和酮在四氯金酸钠三水合物催化下合成 1,5-苯并二氮杂卓的有效而清洁的方法。该催化剂在类似的反应条件下，同样可以有效地从邻苯二胺和α-溴代酮合成喹喔啉。该方法产率良好。
相似文献
1
Sodium tetrachloroaurate(III) dihydrate-catalyzed efficient synthesis of 1,5-benzodiazepine and quinoxaline derivatives.水合三氯金酸钠(III)催化高效合成 1,5-苯并二氮杂卓和喹喔啉衍生物。
J Zhejiang Univ Sci B. 2010 Feb;11(2):102-8. doi: 10.1631/jzus.B0900288.
2
Bismuth (III) Salts Promoted and Ionic Liquid Assisted an Efficient and Environmentally Benign One-Pot Synthesis of 1,5-Benzodiazepine Derivatives.铋（III）盐促进及离子液体辅助的1,5-苯并二氮杂䓬衍生物高效且环境友好的一锅法合成
ISRN Org Chem. 2011 May 14;2011:604348. doi: 10.5402/2011/604348. eCollection 2011.
3
Efficient TCT-catalyzed synthesis of 1,5-benzodiazepine derivatives under mild conditions.在温和条件下高效的TCT催化合成1,5-苯二氮䓬衍生物。
Molecules. 2008 Sep 25;13(9):2313-25. doi: 10.3390/molecules13092313.
4
Synthesis of some 1H-1,5-benzodiazepine Series Containing Chromene Ring from α,β-Unsaturated Ketones of 6-Acetyl-5-Hydroxy-4-Methylcoumarin.由6-乙酰基-5-羟基-4-甲基香豆素的α,β-不饱和酮合成一些含色烯环的1H-1,5-苯并二氮杂䓬系列化合物。
Curr Org Synth. 2020;17(5):404-410. doi: 10.2174/1570179417666200415152105.
5
Gallium (III) triflate-catalyzed synthesis of heterocycles: quinoxalines, 1,5-benzodiazepines and their fluorinated derivatives.三氟甲磺酸镓催化的杂环合成：喹喔啉、1,5-苯并二氮杂䓬及其氟化衍生物。
Future Med Chem. 2009 Aug;1(5):909-20. doi: 10.4155/fmc.09.77.
6
An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using recyclable alumina-supported heteropolyoxometalates.一种使用可回收的氧化铝负载杂多金属氧酸盐在室温下合成喹喔啉衍生物的高效方法。
ScientificWorldJournal. 2012;2012:174784. doi: 10.1100/2012/174784. Epub 2012 Mar 12.
7
Ferrocene anchored activated carbon as a versatile catalyst for the synthesis of 1,5-benzodiazepines one-pot environmentally benign conditions.二茂铁锚定的活性炭作为一种通用催化剂，用于在一锅法环境友好条件下合成1,5-苯二氮䓬。
RSC Adv. 2022 May 17;12(23):14740-14756. doi: 10.1039/d2ra00202g. eCollection 2022 May 12.
8
Efficient Construction of 5H-1,4-Benzodiazepine Derivatives by a Catalyst-Free Direct Aerobic Oxidative Annulation Strategy.无催化剂直接有氧氧化环合策略高效构建 5H-1,4-苯并二氮杂䓬衍生物。
ChemSusChem. 2021 Jul 22;14(14):2866-2871. doi: 10.1002/cssc.202100703. Epub 2021 Jun 18.
9
A green and efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using heteropolyanion-based ionic liquids: as a recyclable solid catalyst.一种使用基于杂多阴离子的离子液体作为可循环使用的固体催化剂合成喹喔啉、苯并恶唑和苯并咪唑衍生物的绿色高效方法。
Comb Chem High Throughput Screen. 2013 Sep;16(8):618-27. doi: 10.2174/1386207311316080004.
10
Eco-friendly approach to access of quinoxaline derivatives using nanostructured pyrophosphate NaPdPO as a new, efficient and reusable heterogeneous catalyst.使用纳米结构焦磷酸盐NaPdPO作为新型、高效且可重复使用的多相催化剂，以环保方式合成喹喔啉衍生物。
BMC Chem. 2020 Feb 3;14(1):6. doi: 10.1186/s13065-020-0662-z. eCollection 2020 Dec.
本文引用的文献
1
Efficient TCT-catalyzed synthesis of 1,5-benzodiazepine derivatives under mild conditions.在温和条件下高效的TCT催化合成1,5-苯二氮䓬衍生物。
Molecules. 2008 Sep 25;13(9):2313-25. doi: 10.3390/molecules13092313.
2
Gold catalysis in total synthesis.全合成中的金催化
Chem Soc Rev. 2008 Sep;37(9):1766-75. doi: 10.1039/b615629k. Epub 2008 Jul 7.
3
Gold-catalyzed organic transformations.金催化的有机转化反应。
Chem Rev. 2008 Aug;108(8):3239-65. doi: 10.1021/cr068434l. Epub 2008 Jul 10.
4
A Au(i)-catalyzed N-acyl iminium ion cyclization cascade.A 金（I）催化的N-酰基亚胺离子环化串联反应。
J Am Chem Soc. 2007 Oct 10;129(40):12070-1. doi: 10.1021/ja074550+. Epub 2007 Sep 18.
5
Gold-catalyzed organic reactions.金催化的有机反应。
Chem Rev. 2007 Jul;107(7):3180-211. doi: 10.1021/cr000436x. Epub 2007 Jun 20.
6
Non-nanogold catalyzed aerobic oxidation of secondary amines to imines.非纳米金催化仲胺有氧氧化生成亚胺。
Chem Commun (Camb). 2007 Jun 7(21):2157-9. doi: 10.1039/b700555e. Epub 2007 May 1.
7
Relativistic effects in homogeneous gold catalysis.均相金催化中的相对论效应。
Nature. 2007 Mar 22;446(7134):395-403. doi: 10.1038/nature05592.
8
Gold catalysis.金催化
Angew Chem Int Ed Engl. 2006 Dec 4;45(47):7896-936. doi: 10.1002/anie.200602454.
9
Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions.在溶液、无溶剂或固相条件下，通过1,2-二氮杂-1,3-丁二烯与1,2-二胺的反应直接合成吡嗪、哌嗪酮和喹喔啉。
J Org Chem. 2006 Aug 4;71(16):5897-905. doi: 10.1021/jo060450v.
10
Manganese(IV) dioxide-catalyzed synthesis of quinoxalines under microwave irradiation.二氧化锰催化微波辐射下喹喔啉的合成
Chem Commun (Camb). 2005 Mar 14(10):1321-3. doi: 10.1039/b417556e. Epub 2005 Jan 20.
Zotero 插件