Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines
N -Sulfonyl derivatives of 1,4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine n...
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| Veröffentlicht in: | Russian journal of organic chemistry 2017, Vol.53 (4), p.525-538 |
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| container_title | Russian journal of organic chemistry |
| container_volume | 53 |
| creator | Konovalova, S. A. Avdeenko, A. P. Pirozhenko, V. V. Yusina, A. L. Palamarchuk, G. V. Shishkina, S. V. |
| description | N
-Sulfonyl derivatives of 1,4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine nitrogen atom, and enamine structure. The presence of strong electron-withdrawing trifluoromethanesulfonyl group on the quinone imine nitrogen atom favors formation of 1,4-addition products and benzofuran derivatives. |
| doi_str_mv | 10.1134/S1070428017040054 |
| format | Article |
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-Sulfonyl derivatives of 1,4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine nitrogen atom, and enamine structure. The presence of strong electron-withdrawing trifluoromethanesulfonyl group on the quinone imine nitrogen atom favors formation of 1,4-addition products and benzofuran derivatives.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428017040054</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Chemistry ; Chemistry and Materials Science ; Derivatives ; Imines ; Nitrogen ; Organic Chemistry ; Quinones ; Review</subject><ispartof>Russian journal of organic chemistry, 2017, Vol.53 (4), p.525-538</ispartof><rights>Pleiades Publishing, Ltd. 2017</rights><rights>Copyright Springer Science & Business Media 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-bf735c4d32e7483c9553647db291a56ece9f0079ba4a9628994c7ed9d6f147983</citedby><cites>FETCH-LOGICAL-c316t-bf735c4d32e7483c9553647db291a56ece9f0079ba4a9628994c7ed9d6f147983</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/S1070428017040054$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428017040054$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Konovalova, S. A.</creatorcontrib><creatorcontrib>Avdeenko, A. P.</creatorcontrib><creatorcontrib>Pirozhenko, V. V.</creatorcontrib><creatorcontrib>Yusina, A. L.</creatorcontrib><creatorcontrib>Palamarchuk, G. V.</creatorcontrib><creatorcontrib>Shishkina, S. V.</creatorcontrib><title>Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>N
-Sulfonyl derivatives of 1,4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine nitrogen atom, and enamine structure. The presence of strong electron-withdrawing trifluoromethanesulfonyl group on the quinone imine nitrogen atom favors formation of 1,4-addition products and benzofuran derivatives.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Derivatives</subject><subject>Imines</subject><subject>Nitrogen</subject><subject>Organic Chemistry</subject><subject>Quinones</subject><subject>Review</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1UEtLAzEQDqJgrf4AbwtejU42s8kGvEjxBUXBx3nJZhPd0iY12SL115taD4J4-mb4HjN8hBwzOGOM4_kTAwlY1sAyAFS4Q0ZMQE05V3w3z5mmG36fHKQ0AwBkyEfk4tFqM_TBF8EV9zSt5i749ZyyU6St9Z_hfdX74G3RL3pvU_HRD2-F9fp7OyR7Ts-TPfrBMXm5vnqe3NLpw83d5HJKDWdioK2TvDLY8dJKrLlRVcUFyq4tFdOVsMYqByBVq1ErUdZKoZG2U51wDKWq-ZicbHOXMf9j09DMwir6fLJhCrCWQmGVVWyrMjGkFK1rlrFf6LhuGDSbkpo_JWVPufWkrPWvNv5K_tf0BZoIZqg</recordid><startdate>2017</startdate><enddate>2017</enddate><creator>Konovalova, S. A.</creator><creator>Avdeenko, A. P.</creator><creator>Pirozhenko, V. V.</creator><creator>Yusina, A. L.</creator><creator>Palamarchuk, G. V.</creator><creator>Shishkina, S. V.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>2017</creationdate><title>Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines</title><author>Konovalova, S. A. ; Avdeenko, A. P. ; Pirozhenko, V. V. ; Yusina, A. L. ; Palamarchuk, G. V. ; Shishkina, S. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-bf735c4d32e7483c9553647db291a56ece9f0079ba4a9628994c7ed9d6f147983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Derivatives</topic><topic>Imines</topic><topic>Nitrogen</topic><topic>Organic Chemistry</topic><topic>Quinones</topic><topic>Review</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Konovalova, S. A.</creatorcontrib><creatorcontrib>Avdeenko, A. P.</creatorcontrib><creatorcontrib>Pirozhenko, V. V.</creatorcontrib><creatorcontrib>Yusina, A. L.</creatorcontrib><creatorcontrib>Palamarchuk, G. V.</creatorcontrib><creatorcontrib>Shishkina, S. 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>Konovalova, S. A.</au><au>Avdeenko, A. P.</au><au>Pirozhenko, V. V.</au><au>Yusina, A. L.</au><au>Palamarchuk, G. V.</au><au>Shishkina, S. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2017</date><risdate>2017</risdate><volume>53</volume><issue>4</issue><spage>525</spage><epage>538</epage><pages>525-538</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>N
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| subjects | Chemistry Chemistry and Materials Science Derivatives Imines Nitrogen Organic Chemistry Quinones Review |
| title | Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines |
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