Tracking the Process of Domino Ring-Opening and Coupling of Fused Imidazole and Direct Observation of Peroxide Intermediates  

作　　者：Yu Wang Mei-Lian Luo Jin Cai Tao Zhang Yu-Jie Wu Ming-Da Song Bin Lu Ming-Hua Zeng 

机构地区：[1]Organic Functional Molecules,College of Chemistry&Chemical Engineering,Hubei University,Wuhan,Hubei 430062,China [2]State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources,Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources(Ministry of Education of China),Collaborative Innovation Centerfor Guangxi Ethnic Medicine,Schoolof Chemistryand Pharmaceutical Sciences,Guangxi Normal University,Guilin,Guangxi 541004,China [3]College of Chemistry and Chemical Engineering,Jinggangshan University,Ji'an,Jiangxi 343000,China

出　　处：《Chinese Journal of Chemistry》2023年第17期2089-2094,共6页中国化学（英文版）

基　　金：supported by the National Science Foundation of China(No.22171075);the NSF of the BAGUI Talent Program of Guangxi Province(No.2019AC26001).

摘　　要：Comprehensive Summary,A domino ring-opening and coupling of imidazolyl annulated heterocycles 1(1a:4-methyl-1-(1-methyl-1H-benzo[d]imidazol-2-yl)-4H-benzo[d]imidazo[1,5-a]imidazole,1b:1-(1,5-dimethyl-1H-benzo[d]imidazol-2-yl)-4,7-dimethyl-4H-benzo[d]imidazo[1,5-a]imidazole)with dioxygen was developed at solvothermal condition,leading to conjugated 1,2-diamidoalkenes derivatives 2((E)-ArCONHArC=CArNHCOAr(Ar:1-methyl-1H-benzo[d]imidazolyl(2a),1,5-dimethyl-1H-benzo[d]imidazolyl(2b)))as single crystals directly.The reaction process was tracked by electrospray ionization mass spectrometry(ESI-HRMS)and a series of reaction intermediates are detected.^(18)O_(2) labeling experiment verified the source of oxygen in 2.Combining evidence from control experiments,nuclear magnetic resonance(NMR)tracking,and crystallography,a seven-step reaction pathway involving oxygen addition,ring opening,Friedel-Crafts alkylation,oxidation,and dehydration was proposed and further supported by DFT calculation.

关 键 词：Domino reaction Process tracking Ring-opening Mass spectrometry Isotopes C-C coupling Density functional calculations 

分 类 号：O62[理学—有机化学]