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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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| Published in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-12, Vol.54 (12), p.1131-1138 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c358t-5247a14f5133eaf3a4f001178410673b8bac189cd2c953802cd7f24fef14123a3 |
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| cites | cdi_FETCH-LOGICAL-c358t-5247a14f5133eaf3a4f001178410673b8bac189cd2c953802cd7f24fef14123a3 |
| container_end_page | 1138 |
| container_issue | 12 |
| container_start_page | 1131 |
| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 54 |
| creator | Cheremnykh, Kirill P. Savel’ev, Viktor А. Shkurko, Oleg P. Shults, Elvira E. |
| description | 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. |
| doi_str_mv | 10.1007/s10593-019-02404-w |
| format | article |
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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%. 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The possibility of carrying out the cross coupling – condensation reaction as a one-pot synthesis is demonstrated.</description><subject>Alkaloids</subject><subject>Benzene</subject><subject>Benzoic acid</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chlorides</subject><subject>Condensation</subject><subject>Coupling (molecular)</subject><subject>Cross coupling</subject><subject>Fragments</subject><subject>Hybrid structures</subject><subject>Organic acids</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Psychotropic drugs</subject><subject>Pyrimidines</subject><subject>Tumors</subject><subject>Universities and colleges</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kM9LwzAUx4MoOKf_gKeC5868JF3S4xj-goEH9RzSNOkyu7QmHaP_vZkVvEkOj_f4fvIeH4RuAS8AY34fARclzTGUOSYMs_x4hmZQcJoLWtBzNMMYlzkFQi7RVYy71HIQbIaqt9EPWxNdzDqbbccquDrbd63Rh9bETHd-UM4732T9GNze1c6bTPk6q91gQm9OXfup2i5hrep7lQg3nEI2qGZv_BCv0YVVbTQ3v3WOPh4f3tfP-eb16WW92uSaFmLIC8K4AmYLoNQoSxWzGANwwQAvOa1EpTSIUtdElwUVmOiaW8KsscCAUEXn6G76tw_d18HEQe66Q_BppSTAl1xgIMuUWkypRrVGOm-7ISidXm32Lh1vrEvzVcFJKZI7ngAyATp0MQZjZZ9EqDBKwPIkX07yZZIvf-TLY4LoBMUU9o0Jf7f8Q30DdOqI3Q</recordid><startdate>20181201</startdate><enddate>20181201</enddate><creator>Cheremnykh, Kirill P.</creator><creator>Savel’ev, Viktor А.</creator><creator>Shkurko, Oleg P.</creator><creator>Shults, Elvira E.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20181201</creationdate><title>Synthesis of hybrid molecules containing pyrimidine and diterpene alkaloid lappaconitine fragments</title><author>Cheremnykh, Kirill P. ; Savel’ev, Viktor А. ; Shkurko, Oleg P. ; Shults, Elvira E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-5247a14f5133eaf3a4f001178410673b8bac189cd2c953802cd7f24fef14123a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkaloids</topic><topic>Benzene</topic><topic>Benzoic acid</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chlorides</topic><topic>Condensation</topic><topic>Coupling (molecular)</topic><topic>Cross coupling</topic><topic>Fragments</topic><topic>Hybrid structures</topic><topic>Organic acids</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Psychotropic drugs</topic><topic>Pyrimidines</topic><topic>Tumors</topic><topic>Universities and colleges</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cheremnykh, Kirill P.</creatorcontrib><creatorcontrib>Savel’ev, Viktor А.</creatorcontrib><creatorcontrib>Shkurko, Oleg P.</creatorcontrib><creatorcontrib>Shults, Elvira E.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cheremnykh, Kirill P.</au><au>Savel’ev, Viktor А.</au><au>Shkurko, Oleg P.</au><au>Shults, Elvira E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of hybrid molecules containing pyrimidine and diterpene alkaloid lappaconitine fragments</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2018-12-01</date><risdate>2018</risdate><volume>54</volume><issue>12</issue><spage>1131</spage><epage>1138</epage><pages>1131-1138</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>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. 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| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2018-12, Vol.54 (12), p.1131-1138 |
| issn | 0009-3122 1573-8353 |
| language | eng |
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| 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 |
| title | Synthesis of hybrid molecules containing pyrimidine and diterpene alkaloid lappaconitine fragments |
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