Heterocyclic analogs of 5,12-naphthacenequinone 9. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones
A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3- f ]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2011-05, Vol.47 (2), p.194-203 |
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| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 47 |
| creator | Nikitina, A. N. Shchekotikhin, A. E. Luzikov, Y. N. Korolev, A. M. Buyanov, V. N. Preobrazhenskaya, M. N. |
| description | A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-
f
]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-
f
]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-
f
]isatin-5,10-diones. Successive halogenation using phosphorus penta-chloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-di-methoxynaphtho[2,3-
f
]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative. |
| doi_str_mv | 10.1007/s10593-011-0740-1 |
| format | Article |
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f
]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-
f
]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-
f
]isatin-5,10-diones. Successive halogenation using phosphorus penta-chloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-di-methoxynaphtho[2,3-
f
]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-011-0740-1</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Acylation ; Chemistry ; Chemistry and Materials Science ; Chlorides ; Dichloropropane ; Heterocyclic compounds ; Organic Chemistry ; Pharmacy ; Telomerase</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2011-05, Vol.47 (2), p.194-203</ispartof><rights>Springer Science+Business Media, Inc. 2011</rights><rights>COPYRIGHT 2011 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c355t-35b97f6ec24e7ffa2ca6e3629f3d893c3d2904d8632a75fc63f257448802390b3</citedby><cites>FETCH-LOGICAL-c355t-35b97f6ec24e7ffa2ca6e3629f3d893c3d2904d8632a75fc63f257448802390b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10593-011-0740-1$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10593-011-0740-1$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,777,781,27905,27906,41469,42538,51300</link.rule.ids></links><search><creatorcontrib>Nikitina, A. N.</creatorcontrib><creatorcontrib>Shchekotikhin, A. E.</creatorcontrib><creatorcontrib>Luzikov, Y. N.</creatorcontrib><creatorcontrib>Korolev, A. M.</creatorcontrib><creatorcontrib>Buyanov, V. N.</creatorcontrib><creatorcontrib>Preobrazhenskaya, M. N.</creatorcontrib><title>Heterocyclic analogs of 5,12-naphthacenequinone 9. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-
f
]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-
f
]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-
f
]isatin-5,10-diones. Successive halogenation using phosphorus penta-chloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-di-methoxynaphtho[2,3-
f
]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.</description><subject>Acylation</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chlorides</subject><subject>Dichloropropane</subject><subject>Heterocyclic compounds</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Telomerase</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kc1KAzEUhYMoWKsP4G7AbVOT3Mn8LEXUCoILdSUSYiZpU9qkJqk4r-BTmzpuBJEsLsk938nlHoROKZlSQurzSAlvARNKMalLgukeGlFeA26Awz4aEUJaDJSxQ3QU4zJfa9qUI_Q500kHr3q1sqqQTq78PBbeFHxCGXZys0gLqbTTb1vrvNNFOy0e0rbrd5q00EXsXS7Rxgx3RdBSJftu03e_nORxOrvWaeE_-sHMP7MJYPNio0zW4fwNyZLsHI_RgZGrqE9-6hg9XV89Xs7w3f3N7eXFHVbAecLAX9vaVFqxUtfGSKZkpaFirYGuaUFBx1pSdk0FTNbcqAoM43VZNg1h0JJXGKOzwXcuV1pYZ3wKUq1tVOICKp4XA5Rk1fQPVT6dXluV5zU2v_8C6ACo4GMM2ohNsGsZekGJ2GUkhoxEzkjsMhI0M2xgYta6uQ5i6bchhxD_gb4AtRmSbg</recordid><startdate>20110501</startdate><enddate>20110501</enddate><creator>Nikitina, A. N.</creator><creator>Shchekotikhin, A. E.</creator><creator>Luzikov, Y. N.</creator><creator>Korolev, A. M.</creator><creator>Buyanov, V. N.</creator><creator>Preobrazhenskaya, M. N.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20110501</creationdate><title>Heterocyclic analogs of 5,12-naphthacenequinone 9. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones</title><author>Nikitina, A. N. ; Shchekotikhin, A. E. ; Luzikov, Y. N. ; Korolev, A. M. ; Buyanov, V. N. ; Preobrazhenskaya, M. N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-35b97f6ec24e7ffa2ca6e3629f3d893c3d2904d8632a75fc63f257448802390b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Acylation</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chlorides</topic><topic>Dichloropropane</topic><topic>Heterocyclic compounds</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Telomerase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nikitina, A. N.</creatorcontrib><creatorcontrib>Shchekotikhin, A. E.</creatorcontrib><creatorcontrib>Luzikov, Y. N.</creatorcontrib><creatorcontrib>Korolev, A. M.</creatorcontrib><creatorcontrib>Buyanov, V. N.</creatorcontrib><creatorcontrib>Preobrazhenskaya, M. N.</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>Nikitina, A. N.</au><au>Shchekotikhin, A. E.</au><au>Luzikov, Y. N.</au><au>Korolev, A. M.</au><au>Buyanov, V. N.</au><au>Preobrazhenskaya, M. N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Heterocyclic analogs of 5,12-naphthacenequinone 9. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2011-05-01</date><risdate>2011</risdate><volume>47</volume><issue>2</issue><spage>194</spage><epage>203</epage><pages>194-203</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-
f
]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-
f
]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-
f
]isatin-5,10-diones. Successive halogenation using phosphorus penta-chloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-di-methoxynaphtho[2,3-
f
]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.</abstract><cop>Boston</cop><pub>Springer US</pub><doi>10.1007/s10593-011-0740-1</doi><tpages>10</tpages></addata></record> |
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| language | eng |
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| subjects | Acylation Chemistry Chemistry and Materials Science Chlorides Dichloropropane Heterocyclic compounds Organic Chemistry Pharmacy Telomerase |
| title | Heterocyclic analogs of 5,12-naphthacenequinone 9. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones |
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