Palladium-Catalyzed C-H Functionalization of Amido-substitued 1,4-Napthoquinone in the Presence of Amines Toward the Formation of Pyrroles and Imidazoles

• Main Authors: Szu-Wei Chen, 陳思暐
• Other Authors: 洪豐裕
• Format: Others
• Language: zh-TW
• Published: 2017
• Online Access: http://ndltd.ncl.edu.tw/handle/69301949949248348912

碩士 === 國立中興大學 === 化學系所 === 105 === 1-H-Benz[f]indole-4,9-diones 3 were prepared in good yields by treating N-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide 2a with tertiary amines and using Pd(OAc)2 as the catalyst precursor in one-pot reactions and the structure of 3c was determined by single crystal X-ray diffraction methods. As revealed from the structure of 3c, the transition metal complex Pd(OAc)2 indeed catalyzed amines and 2a, which led to the formation of pyrrole through cyclization processes by fusing to the former napthoquinone framework. A mechanism was proposed after screening some relevant reaction conditions. Thereafter, similar reactions were carried out by employing primary and secondary amines as the amine sources. When primary amines are used as the reactants, the products will be either imidazolequinones or aminoquinones depending on the extent of the steric hindrance of amines. When secondary amines are used as the reactants, the products will be either indolequinone or aminoquinones again depending on the extent of the steric hindrance of amines. In addition, similar reactions were carried out by replacing tertiary amines with tertiary phosphines which led to the formation of ylide-like derivatives instead.