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- W1997352968 abstract "Aminonaphthochinon 2 ergibt - im Gegensatz zum Isomer 1 (Schema 3) - mit Methyleniminiumsalzen unter kinetischer Kontrolle zunächst Aminalsalze 3-HX - 6-HX, die sich anschließend zu den thermodynamisch stabilen C-Mannich-Verbindungen 7-HX - 10-HX umsetzen. Entsprechende N-substituierte 1,4-Naphthochinone 11 - 13 liefern sofort die 3-Aminomethylsalze 14-HX - 16-HX. Vergleichende Untersuchungen an den isomeren Phenyl-aminochinonen 12 und 17 zeigen - auch bei verschiedenen Aminomethylierungsmethoden - stets eine höhere Reaktivität des 4-Amino-1,2-naphthochinons. Aus den N-primären und sekundären Aminochinonen entstehen mit primärem Amin und 2 Mol Formaldehyd die Tetrahydropyrimidine 23 - 43. 2-Amino-1,2-naphthoquinones and 4-Amino-1,2-naphthoquinones as Nucleophiles - a Comparison Contrary to the behavior of 4-amino-1,2-naphthoquinone (1). 2-amino-1,4-naphthoquinone (2) (Scheme 3) reacts initially with methyleniminium salts by kinetic control to the N-aminomethyl compounds 3-HX - 6-HX, which subsequently generate the thermodynamic stable C-Mannich products 7-HX - 10-HX. Under the same conditions the 2-N-substituted 1,4-naphthoquinones 11 - 13 immediately yield the 3-aminomethyl derivatives 14-HX - 16-HX. Comparative experiments with the isomeric 2-phenylamino-1,4-naphthoquinone (12) and 4-phenylamino-1,2-naphthoquinone (17) using different aminomethylation methods always show a higher reactivity of the ortho-quinonoid compound. A similar reactivity pattern was observed for the cyclization of the N-primary and secondary amino-quinones 1,2, 12, 17 - 22, which produce the tetrahydropyrimidines 23 - 43 with 1 mole of primary amine and 2 moles of formaldehyde." @default.
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- W1997352968 date "1991-01-01" @default.
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- W1997352968 title "2-Amino-1,4-naphthochinone und 4-Amino-1,2-naphthochinone als Nucleophile - ein Vergleich" @default.
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- W1997352968 doi "https://doi.org/10.1002/ardp.19913240307" @default.
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