Synthesis of hybrid molecules containing pyrimidine and diterpene alkaloid lappaconitine fragments

The cross coupling of 5'-ethynyllappaconitine with benzoic acid chlorides under the conditions of the Sonogashira reaction in benzene leads to the corresponding 5-alkynones. By condensation of the obtained 5'-alkynones with amidines, compounds with hybrid structure containing fragments of...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-12, Vol.54 (12), p.1131-1138
Main Authors: Cheremnykh, Kirill P., Savel’ev, Viktor А., Shkurko, Oleg P., Shults, Elvira E.
Format: Article
Language:English
Subjects:
Alkaloids
Benzene
Benzoic acid
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chlorides
Condensation
Coupling (molecular)
Cross coupling
Fragments
Hybrid structures
Organic acids
Organic Chemistry
Pharmacy
Psychotropic drugs
Pyrimidines
Tumors
Universities and colleges
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Summary:The cross coupling of 5'-ethynyllappaconitine with benzoic acid chlorides under the conditions of the Sonogashira reaction in benzene leads to the corresponding 5-alkynones. By condensation of the obtained 5'-alkynones with amidines, compounds with hybrid structure containing fragments of a diterpene alkaloid and pyrimidine were synthesized. The yields of the target compounds were 67–90%. The possibility of carrying out the cross coupling – condensation reaction as a one-pot synthesis is demonstrated.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-019-02404-w