Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates Full article
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Heterocyclic Communications
ISSN: 0793-0283 , E-ISSN: 2191-0197 |
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| Output data | Year: 2017, Volume: 23, Number: 2, Pages: 85-90 Pages count : 6 DOI: 10.1515/hc-2016-0190 | ||
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Abstract:
A new stereoselective cascade reaction of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid by the action of bromine in the presence of a base into substituted (barbituric acid)-5-spirocyclopropanes is described. The yields are in the range of 60%–75%. Nuclear magnetic resonance (NMR) studies indicate that this cascade transformation results in the stereoselective formation of spiro products with trans-configuration of aryl and alkoxycarbonyl substituents in the cyclopropane ring. The products are a perspective class of compounds with prominent pharmacological and physiological activity.
Cite:
Elinson M.N.
, Vereshchagin A.N.
, Korshunov A.D.
, Ryzhkov F.V.
, Egorov M.P.
Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates
Heterocyclic Communications. 2017. V.23. N2. P.85-90. DOI: 10.1515/hc-2016-0190 WOS Scopus OpenAlex
Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates
Heterocyclic Communications. 2017. V.23. N2. P.85-90. DOI: 10.1515/hc-2016-0190 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000397981300004 |
| Scopus: | 2-s2.0-85017288324 |
| OpenAlex: | W2604441483 |