Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin
Aldol-crotonic condensation of allobetulone and betulonic aldehyde with N -substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new α,β-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of...
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| Veröffentlicht in: | Russian journal of organic chemistry 2015-05, Vol.51 (5), p.715-726 |
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| container_title | Russian journal of organic chemistry |
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| creator | Babak, N. L. Semenenko, A. N. Gella, I. M. Musatov, V. I. Shishkina, S. V. Novikova, N. B. Sofronov, D. S. Morina, D. A. Lipson, V. V. |
| description | Aldol-crotonic condensation of allobetulone and betulonic aldehyde with
N
-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new α,β-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1
H
-pyrazole-4-carbaldehyde, (
E
)-2-{[3-(4-methoxyphenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulone, (
E
)-2-{[3-(4-bromophenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (
E
)-2-{[3-(4-bromo-phenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulin, and (
E
)-2-{[3-(4-bromophe-nyl)-1-phenyl-1
H
-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study. |
| doi_str_mv | 10.1134/S1070428015050231 |
| format | Article |
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N
-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new α,β-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1
H
-pyrazole-4-carbaldehyde, (
E
)-2-{[3-(4-methoxyphenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulone, (
E
)-2-{[3-(4-bromophenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (
E
)-2-{[3-(4-bromo-phenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulin, and (
E
)-2-{[3-(4-bromophe-nyl)-1-phenyl-1
H
-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428015050231</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Chemistry ; Chemistry and Materials Science ; Organic Chemistry</subject><ispartof>Russian journal of organic chemistry, 2015-05, Vol.51 (5), p.715-726</ispartof><rights>Pleiades Publishing, Ltd. 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c288t-91b23f7c04013b57adcee0afe7279b2b155fc9b3598c408832191825773a99c3</citedby><cites>FETCH-LOGICAL-c288t-91b23f7c04013b57adcee0afe7279b2b155fc9b3598c408832191825773a99c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428015050231$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428015050231$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,778,782,27911,27912,41475,42544,51306</link.rule.ids></links><search><creatorcontrib>Babak, N. L.</creatorcontrib><creatorcontrib>Semenenko, A. N.</creatorcontrib><creatorcontrib>Gella, I. M.</creatorcontrib><creatorcontrib>Musatov, V. I.</creatorcontrib><creatorcontrib>Shishkina, S. V.</creatorcontrib><creatorcontrib>Novikova, N. B.</creatorcontrib><creatorcontrib>Sofronov, D. S.</creatorcontrib><creatorcontrib>Morina, D. A.</creatorcontrib><creatorcontrib>Lipson, V. V.</creatorcontrib><title>Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>Aldol-crotonic condensation of allobetulone and betulonic aldehyde with
N
-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new α,β-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1
H
-pyrazole-4-carbaldehyde, (
E
)-2-{[3-(4-methoxyphenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulone, (
E
)-2-{[3-(4-bromophenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (
E
)-2-{[3-(4-bromo-phenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulin, and (
E
)-2-{[3-(4-bromophe-nyl)-1-phenyl-1
H
-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kMtqwzAQRUVpoWnaD-jOP6B2Ro9KWpbQFwS6SJYFI8ty46DYQXIC7tdXeewKXc3MvXOG4RJyj_CAyMXjAkGBYBpQggTG8YJM8Ak05dzwy9xnmx78a3KT0hoABAo-IV-LsRtWPrWp6JtiO8bYB8roGGhhu_og2J-siKxs_LAaQ1v7zhe1j-3eDu3eH7nKD7vQdkfEhtCf51ty1diQ_N25Tsny9WU5e6fzz7eP2fOcOqb1QA1WjDfKgQDklVS2dt6DbbxiylSsQikbZyoujXYCtOYMDWomleLWGMenBE9nXexTir4pt7Hd2DiWCOUhnfJPOplhJybl3e7bx3Ld72KXv_wH-gWWPWbQ</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Babak, N. L.</creator><creator>Semenenko, A. N.</creator><creator>Gella, I. M.</creator><creator>Musatov, V. I.</creator><creator>Shishkina, S. V.</creator><creator>Novikova, N. B.</creator><creator>Sofronov, D. S.</creator><creator>Morina, D. A.</creator><creator>Lipson, V. V.</creator><general>Pleiades Publishing</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150501</creationdate><title>Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin</title><author>Babak, N. L. ; Semenenko, A. N. ; Gella, I. M. ; Musatov, V. I. ; Shishkina, S. V. ; Novikova, N. B. ; Sofronov, D. S. ; Morina, D. A. ; Lipson, V. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c288t-91b23f7c04013b57adcee0afe7279b2b155fc9b3598c408832191825773a99c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Babak, N. L.</creatorcontrib><creatorcontrib>Semenenko, A. N.</creatorcontrib><creatorcontrib>Gella, I. M.</creatorcontrib><creatorcontrib>Musatov, V. I.</creatorcontrib><creatorcontrib>Shishkina, S. V.</creatorcontrib><creatorcontrib>Novikova, N. B.</creatorcontrib><creatorcontrib>Sofronov, D. S.</creatorcontrib><creatorcontrib>Morina, D. A.</creatorcontrib><creatorcontrib>Lipson, V. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Babak, N. L.</au><au>Semenenko, A. N.</au><au>Gella, I. M.</au><au>Musatov, V. I.</au><au>Shishkina, S. V.</au><au>Novikova, N. B.</au><au>Sofronov, D. S.</au><au>Morina, D. A.</au><au>Lipson, V. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2015-05-01</date><risdate>2015</risdate><volume>51</volume><issue>5</issue><spage>715</spage><epage>726</epage><pages>715-726</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>Aldol-crotonic condensation of allobetulone and betulonic aldehyde with
N
-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new α,β-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1
H
-pyrazole-4-carbaldehyde, (
E
)-2-{[3-(4-methoxyphenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulone, (
E
)-2-{[3-(4-bromophenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (
E
)-2-{[3-(4-bromo-phenyl)-1-phenyl-1
H
-pyrazol-4-yl]methylidene}allobetulin, and (
E
)-2-{[3-(4-bromophe-nyl)-1-phenyl-1
H
-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428015050231</doi><tpages>12</tpages></addata></record> |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Chemistry Chemistry and Materials Science Organic Chemistry |
| title | Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin |
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