80253-73-2Relevant academic research and scientific papers
5-aminopenta-2,4-dienals: Synthesis, activation towards nucleophiles, molecular modeling and biosynthetic implications in relation to the manzamine alkaloids
Yan, Lok-Hang,Skiredj, Adam,Dory, Yves,Delpech, Bernard,Poupon, Erwan
, p. 4973 - 4984 (2014/08/18)
Substituted 5-aminopentadienals and glutaconaldehydes are key elements postulated in the biosynthesis of the diverse class of manzamine-type alkaloids. The activation of 5-aminopentadienals into electrophilic iminium salts and their subsequent reactivity
Ring cleavage of N-arylpyridinium salts by nucleophiles - Regioselectivity and stereochemistry of the products - Part 1
Moehrle,Niessen
, p. 139 - 145 (2007/10/03)
The N-arylpyridinium salts 1, 5 und 10 generate with hydroxylamine a ring cleavage to the E/Z-oximes of the (2E,4E)-5-aminopentadienals 2, 6 und 11. With the 3-methylpyridinium derivative 12 the described regiospecifity of the reaction with nucleophiles is disproved. The attack by hydroxylamine is realized to a nearly equal degree at C-2 and C-6. As 2-methyl substituted products the E-oximes of (2E,4E)- and (2Z,4E)-5-aminopentadienal result, while as 4-methyl substituted products the E/Z-oximes of (2E,4E)-5-aminopentadienal are generated. Just so with the hydroxide ion as nucleophile from 12 - in contrast to the literature - both position isomer 5-aminopentadienals are formed. They were characterized as 15 and 16. The quaternized product of nicotine 22 shows ring opening with hydroxide ion, not at C-2 as described formerly, but only at 6-position and gives rise to the 4-(N-methylpyrrolidinyl) substituted 5-aminopentadienal 23. By hydroxylamine only the E/Z-oxime mixture of the 4-substituted 5-aminopentadienal 25 is formed, which can be dehydrated to the nitrile 27.
