Synthesis of Spiroheterocyclic Systems from Barbituric Acids and N,N-Disubstituted o-Aminobenzaldehydes |
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Authors: | K. A. Krasnov V. G. Kartsev |
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Affiliation: | (1) Mechnikov St. Petersburg State Medical Academy, Piskarevskii pr. 47, St. Petersburg, 195067, Russia;(2) INTERBIOSKRIN Ltd., Chernogolovka, Moscow oblast, Russia |
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Abstract: | Reactions of barbituric, 1,3-dimethylbarbituric, and 2-thiobarbituric acids with 2-(1-pyrrolidinyl)benzaldehyde, its 6- and 7-membered homologs, and 4-phenylpiperazine and morpholine analogs lead to formation of fused systems with a spirocyclic 2,4,6-trioxopyrimidine fragment. The process involves intermediate formation of labile 5-arylmethylidenebarbituric acids which exhibit t-amino effect and undergo spontaneous isomerization to give the final products. The observed spirocyclizations are characterized by an anomalously high rate.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 6, 2005, pp. 920–925.Original Russian Text Copyright © 2005 by Krasnov, Kartsev. |
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