Benzolactams. 4. Reaction of 3‘,4‘- or 4‘,5‘-Dialkoxy-Substituted 1-(2‘-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams
Treatment of 1-(2‘-bromo-3‘,4‘-dialkoxybenzyl)-1,2,3,4-tetrahydroisoquinoline carbamates, 1a,c, with excess alkyllithium gave 8-oxoberbines, 2a,c, which were successively attacked in situ with another molecule of alkyllithium to give 1,2 and/or 1,4 addition products. A primary alkyllithium, such as...
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| Veröffentlicht in: | Journal of organic chemistry 2000-11, Vol.65 (22), p.7495-7500 |
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| creator | Orito, Kazuhiko Miyazawa, Mamoru Kanbayashi, Ryo Tatsuzawa, Takashi Tokuda, Masao Suginome, Hiroshi |
| description | Treatment of 1-(2‘-bromo-3‘,4‘-dialkoxybenzyl)-1,2,3,4-tetrahydroisoquinoline carbamates, 1a,c, with excess alkyllithium gave 8-oxoberbines, 2a,c, which were successively attacked in situ with another molecule of alkyllithium to give 1,2 and/or 1,4 addition products. A primary alkyllithium, such as MeLi or BuLi, gave a 1,2 addition product, 8-methyleneberbine 9a or 8-butylideneberbine 3a. t-BuLi preferred 1,4 addition, followed by elimination of the alkoxy group, to give 9-tert-butyl-8-oxoberbine 6a or 7c. s-BuLi gave a mixture of 1,2 and 1,4 addition products, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4a and 9-s-butyl-8-oxoberbine 5a. Similar treatments of carbamate 1b having no alkoxy group at its 3‘ position gave 1,2 addition products, 8-butylideneberbine 3b, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4b, and 1-(2‘-pivaloylbenzyl)-1,2,3,4-tetrahydroisoquinoline 6b, in all cases. Reactions of 1a with s-BuMgCl and isoPrMgCl also gave the 1,4 adduct, 5a, and its 9-isoPr analogue, 12a. Treatment of 9a with excess NaBH4 in AcOH gave (±)-coralydine (10b). |
| doi_str_mv | 10.1021/jo000749s |
| format | Article |
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Reaction of 3‘,4‘- or 4‘,5‘-Dialkoxy-Substituted 1-(2‘-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams</title><source>MEDLINE</source><source>ACS Publications</source><creator>Orito, Kazuhiko ; Miyazawa, Mamoru ; Kanbayashi, Ryo ; Tatsuzawa, Takashi ; Tokuda, Masao ; Suginome, Hiroshi</creator><creatorcontrib>Orito, Kazuhiko ; Miyazawa, Mamoru ; Kanbayashi, Ryo ; Tatsuzawa, Takashi ; Tokuda, Masao ; Suginome, Hiroshi</creatorcontrib><description>Treatment of 1-(2‘-bromo-3‘,4‘-dialkoxybenzyl)-1,2,3,4-tetrahydroisoquinoline carbamates, 1a,c, with excess alkyllithium gave 8-oxoberbines, 2a,c, which were successively attacked in situ with another molecule of alkyllithium to give 1,2 and/or 1,4 addition products. A primary alkyllithium, such as MeLi or BuLi, gave a 1,2 addition product, 8-methyleneberbine 9a or 8-butylideneberbine 3a. t-BuLi preferred 1,4 addition, followed by elimination of the alkoxy group, to give 9-tert-butyl-8-oxoberbine 6a or 7c. s-BuLi gave a mixture of 1,2 and 1,4 addition products, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4a and 9-s-butyl-8-oxoberbine 5a. Similar treatments of carbamate 1b having no alkoxy group at its 3‘ position gave 1,2 addition products, 8-butylideneberbine 3b, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4b, and 1-(2‘-pivaloylbenzyl)-1,2,3,4-tetrahydroisoquinoline 6b, in all cases. Reactions of 1a with s-BuMgCl and isoPrMgCl also gave the 1,4 adduct, 5a, and its 9-isoPr analogue, 12a. Treatment of 9a with excess NaBH4 in AcOH gave (±)-coralydine (10b).</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo000749s</identifier><identifier>PMID: 11076607</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Indicators and Reagents ; Isoquinolines - chemical synthesis ; Lactams - chemical synthesis ; Lithium Compounds</subject><ispartof>Journal of organic chemistry, 2000-11, Vol.65 (22), p.7495-7500</ispartof><rights>Copyright © 2000 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-2b4ebfba5cb2d15819611a298554c2c623fb5d603b323366967ac00c61344feb3</citedby><cites>FETCH-LOGICAL-a349t-2b4ebfba5cb2d15819611a298554c2c623fb5d603b323366967ac00c61344feb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo000749s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo000749s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11076607$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Orito, Kazuhiko</creatorcontrib><creatorcontrib>Miyazawa, Mamoru</creatorcontrib><creatorcontrib>Kanbayashi, Ryo</creatorcontrib><creatorcontrib>Tatsuzawa, Takashi</creatorcontrib><creatorcontrib>Tokuda, Masao</creatorcontrib><creatorcontrib>Suginome, Hiroshi</creatorcontrib><title>Benzolactams. 4. Reaction of 3‘,4‘- or 4‘,5‘-Dialkoxy-Substituted 1-(2‘-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Treatment of 1-(2‘-bromo-3‘,4‘-dialkoxybenzyl)-1,2,3,4-tetrahydroisoquinoline carbamates, 1a,c, with excess alkyllithium gave 8-oxoberbines, 2a,c, which were successively attacked in situ with another molecule of alkyllithium to give 1,2 and/or 1,4 addition products. A primary alkyllithium, such as MeLi or BuLi, gave a 1,2 addition product, 8-methyleneberbine 9a or 8-butylideneberbine 3a. t-BuLi preferred 1,4 addition, followed by elimination of the alkoxy group, to give 9-tert-butyl-8-oxoberbine 6a or 7c. s-BuLi gave a mixture of 1,2 and 1,4 addition products, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4a and 9-s-butyl-8-oxoberbine 5a. Similar treatments of carbamate 1b having no alkoxy group at its 3‘ position gave 1,2 addition products, 8-butylideneberbine 3b, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4b, and 1-(2‘-pivaloylbenzyl)-1,2,3,4-tetrahydroisoquinoline 6b, in all cases. Reactions of 1a with s-BuMgCl and isoPrMgCl also gave the 1,4 adduct, 5a, and its 9-isoPr analogue, 12a. Treatment of 9a with excess NaBH4 in AcOH gave (±)-coralydine (10b).</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Indicators and Reagents</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Lactams - chemical synthesis</subject><subject>Lithium Compounds</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1DAQxy0EoqVw4AWQLyAqxYu_0xy3hfKhRaB24RrZiaN114mL7YiGE4_Bo3HmSXC0q9IDF3tG8_P_P-MB4CnBC4IpeXXlMcYlr-I9cEgExUhWmN8HhxhTihiV7AA8ivEqQ1gI8RAcEIJLKXF5CH6fmuGHd6pJqo8LyBfwwuTE-gH6DrI_P38VPB8I-gDnoBBz9toqt_U3E7ocdUw2jcm0kKCXdC6eBt97nWUnd4woMmmTyUYF7YfJIVLQghUcJZOC2kxt8Db6b6MdvLODifC7TRu4dNvJuRzZsV_A_ASqIRsUHC7b1s7dxbm9uxhMHt6d5TF40CkXzZP9fQS-nL9Zn71Dq09v358tV0gxXiVENTe600o0mrZEnJBKEqJodSIEb2gjKeu0aCVmmlHGpKxkqRqMG0kY553R7Ai82OlehzyGianubWyMc2owfox1STkhnJEMHu_AJvgYg-nq62B7Faaa4HpeY327xsw-24uOujftP3K_twygHWBjMje3dRW2tSxZKer158v6vPxw8fHritfrzD_f8aqJ2WcMQ_6T_xj_BT_2t9s</recordid><startdate>20001103</startdate><enddate>20001103</enddate><creator>Orito, Kazuhiko</creator><creator>Miyazawa, Mamoru</creator><creator>Kanbayashi, Ryo</creator><creator>Tatsuzawa, Takashi</creator><creator>Tokuda, Masao</creator><creator>Suginome, Hiroshi</creator><general>American Chemical Society</general><scope>BSCLL</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>7X8</scope></search><sort><creationdate>20001103</creationdate><title>Benzolactams. 4. Reaction of 3‘,4‘- or 4‘,5‘-Dialkoxy-Substituted 1-(2‘-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams</title><author>Orito, Kazuhiko ; Miyazawa, Mamoru ; Kanbayashi, Ryo ; Tatsuzawa, Takashi ; Tokuda, Masao ; Suginome, Hiroshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-2b4ebfba5cb2d15819611a298554c2c623fb5d603b323366967ac00c61344feb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Indicators and Reagents</topic><topic>Isoquinolines - chemical synthesis</topic><topic>Lactams - chemical synthesis</topic><topic>Lithium Compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Orito, Kazuhiko</creatorcontrib><creatorcontrib>Miyazawa, Mamoru</creatorcontrib><creatorcontrib>Kanbayashi, Ryo</creatorcontrib><creatorcontrib>Tatsuzawa, Takashi</creatorcontrib><creatorcontrib>Tokuda, Masao</creatorcontrib><creatorcontrib>Suginome, Hiroshi</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Orito, Kazuhiko</au><au>Miyazawa, Mamoru</au><au>Kanbayashi, Ryo</au><au>Tatsuzawa, Takashi</au><au>Tokuda, Masao</au><au>Suginome, Hiroshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Benzolactams. 4. Reaction of 3‘,4‘- or 4‘,5‘-Dialkoxy-Substituted 1-(2‘-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2000-11-03</date><risdate>2000</risdate><volume>65</volume><issue>22</issue><spage>7495</spage><epage>7500</epage><pages>7495-7500</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Treatment of 1-(2‘-bromo-3‘,4‘-dialkoxybenzyl)-1,2,3,4-tetrahydroisoquinoline carbamates, 1a,c, with excess alkyllithium gave 8-oxoberbines, 2a,c, which were successively attacked in situ with another molecule of alkyllithium to give 1,2 and/or 1,4 addition products. A primary alkyllithium, such as MeLi or BuLi, gave a 1,2 addition product, 8-methyleneberbine 9a or 8-butylideneberbine 3a. t-BuLi preferred 1,4 addition, followed by elimination of the alkoxy group, to give 9-tert-butyl-8-oxoberbine 6a or 7c. s-BuLi gave a mixture of 1,2 and 1,4 addition products, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4a and 9-s-butyl-8-oxoberbine 5a. Similar treatments of carbamate 1b having no alkoxy group at its 3‘ position gave 1,2 addition products, 8-butylideneberbine 3b, 1-[2‘-(2‘ ‘-methylbutyryl)benzyl]-1,2,3,4-tetrahydroisoquinoline 4b, and 1-(2‘-pivaloylbenzyl)-1,2,3,4-tetrahydroisoquinoline 6b, in all cases. Reactions of 1a with s-BuMgCl and isoPrMgCl also gave the 1,4 adduct, 5a, and its 9-isoPr analogue, 12a. Treatment of 9a with excess NaBH4 in AcOH gave (±)-coralydine (10b).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11076607</pmid><doi>10.1021/jo000749s</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2000-11, Vol.65 (22), p.7495-7500 |
| issn | 0022-3263 1520-6904 |
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| source | MEDLINE; ACS Publications |
| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Indicators and Reagents Isoquinolines - chemical synthesis Lactams - chemical synthesis Lithium Compounds |
| title | Benzolactams. 4. Reaction of 3‘,4‘- or 4‘,5‘-Dialkoxy-Substituted 1-(2‘-Bromobenzyl)-2-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinolines with Alkyllithium. 1,2 and 1,4 Additions of Alkyllithium to Benzolactams |
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