Abstract
We studied the hydrazide compounds of the α-azidoacetyl group, which showed specific click reactivity by the intramolecular hydrogen bonding between the azido group and the N-H of the hydrazide moiety. In the competitive click reactions with a general alkyl azide, both traceless and non-traceless Staudinger-Bertozzi ligation occurred azide-site-selectively by the acceleration effect of the hydrogen bonding. However, the product obtained from the traceless reaction was further transformed into heterocyclic compounds. In addition, in an attempt at a synthesis of naphthalimide-possessing azidoacetyl hydrazide, nitrogen-nitrogen bond cleavage of the azidoacetyl hydrazides occurred to give the reduced amine product. These unexpected results could help design molecules for the successful Staudinger-Bertozzi ligation of the hydrazide compounds and develop a new nitrogen-nitrogen bond cleavage method.
Original language | English |
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Pages (from-to) | 520-533 |
Number of pages | 14 |
Journal | Organics |
Volume | 3 |
Issue number | 4 |
DOIs | |
State | Published - 2022/12 |
Keywords
- click chemistry
- hydrogen-bonding interaction
- nitrogen-nitrogen bond cleavage
- organic azides
- staudinger ligation
ASJC Scopus subject areas
- Organic Chemistry