Synfacts 2006(5): 0438-0438  
DOI: 10.1055/s-2006-934360
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Hydroamination Route to Heterocycles

Contributor(s): Victor Snieckus, Oleg M. Demchuk
A. Zulys, M. Dochnahl, D. Hollmann, K. Löhnwitz, J.-S. Herrmann, P. W. Roesky*, S. Blechert*
Freie Universität Berlin and Technische Universität Berlin, Germany
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Publikationsverlauf

Publikationsdatum:
21. April 2006 (online)

Significance

Intramolecular cyclizative hydroamination of unactivated double and triple bonds under inexpensive zinc-based catalysis is reported. The illustrated catalyst shows excellent solubility in most organic solvents, air and moisture stability, low toxicity and is compatible with a variety of polar functional groups such as ethers, amides and hydroxylamines to give products in excellent, often quantitative yields. Thus, dihydropyridones A and B, dihydropyrrole N-oxides C, tetrahydro-oxazepines D, dihydrooxazines and dihydropyrazines are obtained in excellent conversion. The absence of co-catalyst {[PhNMe2H][B(C6F5)4]} led to the formation of exocyclic double bond isomer A as the major product. On the other hand, the ­dihydropyridone B was observed when an equal amount of the co-catalyst was added. Similarly, the intramolecular hydroamination of non-activated alkenes (e.g., 2-methylpent-4-en-1-amine) was also accomplished.