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通过分子内C(sp2)−H羰基化反应合成4(3H)-喹唑啉酮类化合物
Alternative TitleSynthesis of Quinazolin-4(3H)-ones via Pd(II)-Catalyzed Intramolecular C(sp2)−H Carboxamidation of N-arylamidines
马彬
Subtype硕士
Thesis Advisor朱强 ; 邱发洋
2011-07-12
Degree Grantor中国科学院研究生院
Place of Conferral广州生物院
Degree Name硕士
Degree Discipline药物化学
Keyword4(3H)-喹唑啉酮 羰基化反应 C− H活化 Pd催化
Abstract我们发展了一种通过Pd(II)催化的C(sp2)−H键活化、CO插入、分子内酰胺化反应合成4(3H)-喹唑啉酮类化合物的新方法。该方法以简单的未官能化的N-芳基脒为原料,催化量的Pd(OAc)2为催化剂,一当量的CuO为氧化剂,以HOAc为溶剂,在一个大气压的CO气体环境中能够以中等到较好的收率得到4(3H)-喹唑啉酮类化合物。富电子的N-芳基脒对反应有利,但是缺电子的底物不能得到相应的产物。反应原料N-芳基脒可以从苯胺和芳香或脂肪腈一步加成得到。从底物适用范围和同位素标记反应结果可以推测, 作为关键步骤的C(sp2)−H键活化是通过配位金属对芳环的亲电芳基取代(SEAr)来实现的。和已知的合成4(3H)-喹唑啉酮类化合物的方法比较,该方法具有原子经济性和反应步骤短等优点。但是,该方法对吸电子取代基取代的4(3H)-喹唑啉酮类化合物不适用。
Other AbstractAn new efficient synthesis of quinazolin-4(3H)-ones, through palladium- catalyzed intramolecular C(sp2)−H carboxamidation, has been developed. The reaction carried out in the presence of 1.0 equivalent of CuO as oxidant under atmospheric pressure of CO, provides diversified 2-aryl(alkyl)quinazolin-4(3H)-ones in reasonable to good yields from N-arylamidines. Electron-rich N-arylamidines is good for the reaction, while electron-deficient N-arylamidines is not. Starting materials, N-arylamidines can be readily derived from anilines and nitriles by one-step addition. We can speculate a mechanism of the reaction as a SEAr procedure, for the scope of sbustrate and isotopic experiment. Compared with existing approaches to quinazolin-4(3H)-ones, the current strategy features atom-economy and step-efficiency. But this methed is not suitable for electron-deficient substrates.
Subject Area药物化学
Pages86
Language中文
Document Type学位论文
Identifierhttp://ir.foo.ac.cn/handle/2SETSVCV/979
Collection中国科学院广州生物医药与健康研究院
Affiliation中国科学院广州生物医药与健康研究院
First Author AffilicationGUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH,CHINESE ACADEMY OF SCIENCES
Recommended Citation
GB/T 7714
马彬. 通过分子内C(sp2)−H羰基化反应合成4(3H)-喹唑啉酮类化合物[D]. 广州生物院. 中国科学院研究生院,2011.
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