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Azomethine
imines can be accessed upon heating appropriate alkynylhydrazide precursors.
This simple thermal hydroamination approach allows the formation of
five- and six-membered dipoles in modest to excellent yields. The
structure of the acyl group is important to minimize side reactions
and allow the isolation of the azomethine imines by column chromatography.
Ring closure reactions O 0130Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation. -N-Benzoyl hydrazides undergo Cope-type intramolecular hydroaminations to give five-, six-, and seven-membered N-benzoylamino-N-heterocycles. Analogous N-Boc-and N-carbamoyl hydrazides under microwave irradiation are intramolecularly aminocarbonylated to give bicyclic pyrazoles. -(ROVEDA, J.-G.; CLAVETTE, C.; HUNT, A. D.; GORELSKY, S. I.; WHIPP, C. J.; BEAUCHEMIN*, A. M.; J. Am. Chem. Soc. 131 (2009) 25, 8740-8741; Dep. Chem., Univ. Ottawa, Ottawa, Ont. K1N 6N5, Can.; Eng.) -Klein 48-040
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