Ipso-Substitution in Derivatives of the Quinoline Alkaloid Skimmianine
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DOI: 10.1007/s10600-021-03398-8
Abstract: Oxidation of the alkaloid skimmianine produced a formyl derivative that reacted with homoveratrylamine to give the product of nucleophilic ipso-substitution 3-formyl-4-(3,4-dimethoxyphenylethylamino)-7,8- dimethoxyquinolin-2-one. The presence of the formyl group in the latter stimulated its further ipso-substitution… read more here.
Keywords: alkaloid skimmianine; ipso substitution; derivatives quinoline; substitution derivatives ... See more keywords
Reaction of 2,5-dihydroxy-[1,4]-benzoquinone with nucleophiles - ipso-substitution vs. addition/elimination.
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DOI: 10.1039/d0cc04748a
Abstract: 2,5-Dihydroxy-[1,4]-benzoquinone (DHBQ) reacts readily with secondary amines to 2,5-diamino compounds and with thiols to the corresponding 2,5-dithioether derivatives. The literature has been inconclusive about the detailed mechanism, as both ipso-substitution at C-2/C-5 and the sequence… read more here.
Keywords: addition elimination; reaction; ipso substitution;