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2005
Ring closure reactions
O 0130
tert-Amino Effect in Heterocyclic Chemistry. Synthesis of Hydrogenated Spiro
of Quinolines. — The synthesis of spiro derivatives of heterocycles is
09- 029 Derivatives
based on reactions proceeding by the mechanism of the "tert-amino-effect" which generalizes cyclization reactions of certain derivatives of ortho-substituted N,N-dialkylanilines. Using this strategy, a variety of spiro compounds is obtained by reaction of
o-aminobenzaldehydes (III) with cyclic CH-active compounds such as (IV), (VI),
(VIII), and (X). A further method involves Koevenagel condensation of (III) with
malonic ester, cyclization of the resulting benzylidenemalonic esters to fused quinolines, and condensation of the latter with disubstituted urea to afford the targets. However, this method involves disadvantages associated with the formation of by-products.
— (D'YACHENKO, E. V.; GLUKHAREVA, T. V.; NIKOLAENKO, E. F.; TKACHEV,
A. V.; MORZHERIN*, Y. Y.; Russ. Chem. Bull. 53 (2004) 6, 1240-1247; Urals State
Tech. Univ., Ekaterinburg 620002, Russia; Eng.) — H. Hoennerscheid
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