Synthesis of 3-(aminomethyl)pyridine by traceless C3-selective umpolung of 1-amidopyridin-1-ium salts

A natural product inspired rapid access of 3-(aminomethyl)pyridine by one-pot reaction of 1-amidopyridin-1-ium salt with aminal followed by reductive cleavage of the N-N bond is developed. This C3-selective formal C-H activation of pyridine features a traceless umpolung of the 1-amidopyridin-1-ium s...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017-02, Vol.53 (12), p.1993-1996
Main Authors: Tang, Pingsheng, Xiao, Dehai, Wang, Bo
Format: Article
Language:English
Subjects:
Activation
Bonding
Carbon-carbon composites
Chemical bonds
Cleavage
Natural products
Pyridines
Synthesis
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Summary:A natural product inspired rapid access of 3-(aminomethyl)pyridine by one-pot reaction of 1-amidopyridin-1-ium salt with aminal followed by reductive cleavage of the N-N bond is developed. This C3-selective formal C-H activation of pyridine features a traceless umpolung of the 1-amidopyridin-1-ium salt toward a Mannich type C-C bond formation of the in situ generated 1-amido-2-dialkylamino-1,2-dihydropyridine intermediate.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc09582h