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Tertiary amines as vinyl source for the formations of aryl or pyrrole ring on amido‐substitued 1,4‐quinone with the assistance of palladium salt
Journal of the Chinese Chemical Society ( IF 1.8 ) Pub Date : 2020-06-09 , DOI: 10.1002/jccs.202000122
Jia‐Nan Jhou, Chiu‐Wen Cheng, Fung‐E Hong

The one‐pot synthesis of 3‐isopropyl‐6‐methyl‐1H‐benzo[f]indole‐4,9‐dione (3e), N‐(4‐[isopentylamino]‐3,6‐dioxocyclohexa‐1,4‐dien‐1‐yl)acetamide (4d), 2‐(isopentylamino)‐6‐methylnaphthalene‐1,4‐dione (5b), and 2‐(4‐acetamido‐3,6‐dioxocyclohexa‐1,4‐dien‐1‐yl)‐N,N‐diisopentyl‐3‐methylbutanamide (6a) has been achieved via either pyrrol/aryl ring formations or amination reactions from the Pd(II)‐catalyzed reaction of N‐(3,6‐dioxocyclohexa‐1,4‐dien‐1‐yl)acetamide (2a_BQ) and in the presence of triisopentylamine. More 3‐, 4‐, 5‐, and 6‐like derivatives were obtained while other trialkylamines were used. Crystal structures of 3d_O, 3e, 4b, 4c, 4d, 5b, and 6a were determined by single‐crystal X‐ray diffraction methods. The 3‐ and 5‐like products reveal the formations of newly generated benzene rings with/without substitutions. The formation of 6a also implies an unusual reaction pathway of its generation. Based on the structural conformations of various 3‐like products, as well as 6a, mechanisms were proposed to account for the formations of these compounds. Various fascinating conformations of products observed in this work demonstrate the diversities of this type of reactions.

中文翻译:

叔胺作为乙烯基源,借助钯盐在酰胺基取代的1,4-醌上形成芳基或吡咯环

一锅合成3-异丙基-6-甲基-1H-苯并[f]吲哚-4,9-二酮(3e),N-(4- [异戊基氨基] -3,6-二氧代环己基-1,4-二烯-1-基)乙酰胺(4d),2-(异戊基氨基)-6-甲基萘-1,4-二酮(5b)和2-(4-乙酰胺基-3,6-二氧代环己基-1,4-二烯基通过吡咯/芳基环的形成或N-(3,6-二氧代环己基-1的Pd(II)催化反应的胺化反应获得了1-yl)-NN - N-二异戊基-3-甲基丁酰胺6a),4-二烯-1-基)乙酰胺(2a_BQ)并在三异戊胺存在下。更3 - , - 4 - , - 5 - ,和获得了6样衍生物,同时使用了其他三烷基胺。的晶体结构3d_O3E4B4C4D5B,图6A是由单晶X射线衍射方法测定的。的3 -和5 -样产品揭示与/新生成的苯环的结构,而不取代。6a的形成也暗示了其生成的异常反应途径。基于各种3类产品以及6a的结构构象提出了机制来解释这些化合物的形成。在这项工作中观察到的各种令人着迷的产物构象证明了这类反应的多样性。
更新日期:2020-06-09
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