Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8, 14-Cycloberbines
A simple and convenient transformation of berberine (1) into trans-, cis-, and unsaturated benzindenoazepines through regioselective C14-N bond cleavage of 8, 14-cycloberbines is described. Acidic treatment of the 8, 14-cycloberbine (2) effected regioselective ring opening to afford the trans-and ci...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1985/04/25, Vol.33(4), pp.1434-1443 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | HANAOKA, MIYOJI KIM, SINKYU INOUE, MITSURU NAGAMI, KAZUYOSHI SHIMADA, YASUJI YASUDA, SHINGO |
| description | A simple and convenient transformation of berberine (1) into trans-, cis-, and unsaturated benzindenoazepines through regioselective C14-N bond cleavage of 8, 14-cycloberbines is described. Acidic treatment of the 8, 14-cycloberbine (2) effected regioselective ring opening to afford the trans-and cis-benzindenoazepines (7a and 7b) as the kinetically and thermodynamically controlled products, respectively. Dehydration of their N-methyl derivatives (11a and 11b) gave the unsaturated benzindenoazepine (20), which was obtained more efficiently from the 8, 14-cycloberbine (2) by treatment with p-toluenesulfonic acid in benzene followed by N-methylation. Similarly, the ring D-inverted 8, 14-cycloberbine (23) was converted to the corresponding trans-, cis-, and unsaturated benzindenoazepines (24a, 24b, and 27, respectively). |
| doi_str_mv | 10.1248/cpb.33.1434 |
| format | Article |
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Acidic treatment of the 8, 14-cycloberbine (2) effected regioselective ring opening to afford the trans-and cis-benzindenoazepines (7a and 7b) as the kinetically and thermodynamically controlled products, respectively. Dehydration of their N-methyl derivatives (11a and 11b) gave the unsaturated benzindenoazepine (20), which was obtained more efficiently from the 8, 14-cycloberbine (2) by treatment with p-toluenesulfonic acid in benzene followed by N-methylation. 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VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8, 14-Cycloberbines</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A simple and convenient transformation of berberine (1) into trans-, cis-, and unsaturated benzindenoazepines through regioselective C14-N bond cleavage of 8, 14-cycloberbines is described. Acidic treatment of the 8, 14-cycloberbine (2) effected regioselective ring opening to afford the trans-and cis-benzindenoazepines (7a and 7b) as the kinetically and thermodynamically controlled products, respectively. Dehydration of their N-methyl derivatives (11a and 11b) gave the unsaturated benzindenoazepine (20), which was obtained more efficiently from the 8, 14-cycloberbine (2) by treatment with p-toluenesulfonic acid in benzene followed by N-methylation. Similarly, the ring D-inverted 8, 14-cycloberbine (23) was converted to the corresponding trans-, cis-, and unsaturated benzindenoazepines (24a, 24b, and 27, respectively).</description><subject>Benzazepines - chemical synthesis</subject><subject>Berberine - analogs & derivatives</subject><subject>Berberine - analysis</subject><subject>Berberine Alkaloids - chemical synthesis</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Indenes - chemical synthesis</subject><subject>Organic chemistry</subject><subject>p-toluenesulfonic acid-benzene</subject><subject>Preparations and properties</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1985</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU2LFDEQhhtR1nH15FkIKF6028pHf-So7aoDC3pYvYZ0puJm6E7GpGdh9xf4s03vDCOIEBKo90lVwVMUzylUlInundkNFecVFVw8KFaUi7asGeMPixUAyJLxhj8unqS0BWA1tPysOBMgGGOwKn731zg5o0dyFbVPNsRJzy54Eiz5FsMcBoz5OI-pIj_W64pcWOuMQz-TPvgbjOn_NHF-DuQD-jvnN-iDvsPdff3GadK9JVSU_a0Z738s9afFI6vHhM-O73nx_dPFVf-lvPz6ed2_vyyNYCBKlLapaQuWbVhtKaBuGO0GyaCVQzvoBhhnVm-Y7equ5XygII1ERg0MA1DOz4vXh767GH7tMc1qcsngOGqPYZ9U2_C2a2qRwZf_gNuwjz7vpqhoAIQE0WbqzYEyMaQU0apddJOOt4qCWuyobEdxrhY7mX5x7LkfJtyc2KOOnL865jplJzYrMS6dMMlYLSnN2McDtk2z_omnXMfZmRGXkVTW3TJWHK5l-t_4WkeFnv8B0oyvDA</recordid><startdate>19850425</startdate><enddate>19850425</enddate><creator>HANAOKA, MIYOJI</creator><creator>KIM, SINKYU</creator><creator>INOUE, MITSURU</creator><creator>NAGAMI, KAZUYOSHI</creator><creator>SHIMADA, YASUJI</creator><creator>YASUDA, SHINGO</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>19850425</creationdate><title>Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8, 14-Cycloberbines</title><author>HANAOKA, MIYOJI ; KIM, SINKYU ; INOUE, MITSURU ; NAGAMI, KAZUYOSHI ; SHIMADA, YASUJI ; YASUDA, SHINGO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4204-e9f65170f2d25f10ea6218b92079b7ba60232fad2f858733b109c9e21c0bb0133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1985</creationdate><topic>Benzazepines - chemical synthesis</topic><topic>Berberine - analogs & derivatives</topic><topic>Berberine - analysis</topic><topic>Berberine Alkaloids - chemical synthesis</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Indenes - chemical synthesis</topic><topic>Organic chemistry</topic><topic>p-toluenesulfonic acid-benzene</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>HANAOKA, MIYOJI</creatorcontrib><creatorcontrib>KIM, SINKYU</creatorcontrib><creatorcontrib>INOUE, MITSURU</creatorcontrib><creatorcontrib>NAGAMI, KAZUYOSHI</creatorcontrib><creatorcontrib>SHIMADA, YASUJI</creatorcontrib><creatorcontrib>YASUDA, SHINGO</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>HANAOKA, MIYOJI</au><au>KIM, SINKYU</au><au>INOUE, MITSURU</au><au>NAGAMI, KAZUYOSHI</au><au>SHIMADA, YASUJI</au><au>YASUDA, SHINGO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8, 14-Cycloberbines</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1985-04-25</date><risdate>1985</risdate><volume>33</volume><issue>4</issue><spage>1434</spage><epage>1443</epage><pages>1434-1443</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>A simple and convenient transformation of berberine (1) into trans-, cis-, and unsaturated benzindenoazepines through regioselective C14-N bond cleavage of 8, 14-cycloberbines is described. Acidic treatment of the 8, 14-cycloberbine (2) effected regioselective ring opening to afford the trans-and cis-benzindenoazepines (7a and 7b) as the kinetically and thermodynamically controlled products, respectively. Dehydration of their N-methyl derivatives (11a and 11b) gave the unsaturated benzindenoazepine (20), which was obtained more efficiently from the 8, 14-cycloberbine (2) by treatment with p-toluenesulfonic acid in benzene followed by N-methylation. Similarly, the ring D-inverted 8, 14-cycloberbine (23) was converted to the corresponding trans-, cis-, and unsaturated benzindenoazepines (24a, 24b, and 27, respectively).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>4042220</pmid><doi>10.1248/cpb.33.1434</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Benzazepines - chemical synthesis Berberine - analogs & derivatives Berberine - analysis Berberine Alkaloids - chemical synthesis Chemical Phenomena Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Indenes - chemical synthesis Organic chemistry p-toluenesulfonic acid-benzene Preparations and properties |
| title | Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8, 14-Cycloberbines |
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