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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
Author(s) -
Jhou JiaNan,
Cheng ChiuWen,
Hong FungE
Publication year - 2020
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202000122
Subject(s) - chemistry , acetamide , ring (chemistry) , pyrrole , aryl , isopropyl , amination , indole test , benzene , medicinal chemistry , single crystal , crystal structure , stereochemistry , palladium , salt (chemistry) , cyclohexane conformation , catalysis , molecule , crystallography , organic chemistry , alkyl , hydrogen bond
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.