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2005
Multi-membered O,N,S-heterocycles
R 0692
Oxidative Reactions of Azines. Part 11. The Influence of Manganese Dioxide on
Reaction of Tetrahydropyridines with Formaldehyde: Synthesis and Molecu08- 180 the
lar Structures of 3-Oxa-7-azabicyclo[3.3.1]nonane and 6-Oxa-2-azabicyclo[3.2.1]octanes. — Classical Prins-reaction of tetrahydropyridines (I)
with formaldehyde provides the new 3-oxa-7-azabicyclononanes (IV)/(V) along with
known dioxane (VI) and its derivative (VII). Similar condensation of (I) with formaldehyde in the presence of MnO2 alters the direction of the reaction sharply furnishing
6-oxa-2-azabicyclooctanones (III). — (SOLDATENKOV, A. T.; POLYANSKII, K. B.;
TEMESGEN, A. V.; SERGEEVA, N. D.; VYSOTSKAYA, V. V.; AVERKIEV, B. B.;
ANTIPIN, M. Y.; LOBANOV, N. N.; Chem. Heterocycl. Compd. (N. Y.) 40 (2004) 5,
641-649; Russ. Peoples' Friendship Univ., Moscow 117198, Russia; Eng.) —
H. Toeppel
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