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An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction
A novel and efficient annulation of pentane-2,4-dione with 2-(2-bromophenyl)quinazolin-4(3 H )-one was disclosed in DMF catalyzed by CuI/ l -proline in the presence of Cs 2 CO 3 . This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synt...
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| Published in: | Monatshefte für Chemie 2019-07, Vol.150 (7), p.1305-1315 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c356t-1c594aab5d9e27db9ec07e1cdd2829e1be8b6a951f8791a3580f25c984705a263 |
| container_end_page | 1315 |
| container_issue | 7 |
| container_start_page | 1305 |
| container_title | Monatshefte für Chemie |
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| creator | Miao, Wei-Qing Liu, Jian-Quan Wang, Xiang-Shan |
| description | A novel and efficient annulation of pentane-2,4-dione with 2-(2-bromophenyl)quinazolin-4(3
H
)-one was disclosed in DMF catalyzed by CuI/
l
-proline in the presence of Cs
2
CO
3
. This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8
H
-isoquinolino[1,2-
b
]quinazolin-8-ones in good yields.
Graphical abstract |
| doi_str_mv | 10.1007/s00706-019-02430-6 |
| format | article |
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H
)-one was disclosed in DMF catalyzed by CuI/
l
-proline in the presence of Cs
2
CO
3
. This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8
H
-isoquinolino[1,2-
b
]quinazolin-8-ones in good yields.
Graphical abstract</description><identifier>ISSN: 0026-9247</identifier><identifier>EISSN: 1434-4475</identifier><identifier>DOI: 10.1007/s00706-019-02430-6</identifier><language>eng</language><publisher>Vienna: Springer Vienna</publisher><subject>Analytical Chemistry ; Carbonyls ; Chemical reactions ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Dehydration ; Diketones ; Inorganic Chemistry ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Proline ; Theoretical and Computational Chemistry</subject><ispartof>Monatshefte für Chemie, 2019-07, Vol.150 (7), p.1305-1315</ispartof><rights>Springer-Verlag GmbH Austria, part of Springer Nature 2019</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-1c594aab5d9e27db9ec07e1cdd2829e1be8b6a951f8791a3580f25c984705a263</citedby><cites>FETCH-LOGICAL-c356t-1c594aab5d9e27db9ec07e1cdd2829e1be8b6a951f8791a3580f25c984705a263</cites><orcidid>0000-0002-0077-7819</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Miao, Wei-Qing</creatorcontrib><creatorcontrib>Liu, Jian-Quan</creatorcontrib><creatorcontrib>Wang, Xiang-Shan</creatorcontrib><title>An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction</title><title>Monatshefte für Chemie</title><addtitle>Monatsh Chem</addtitle><description>A novel and efficient annulation of pentane-2,4-dione with 2-(2-bromophenyl)quinazolin-4(3
H
)-one was disclosed in DMF catalyzed by CuI/
l
-proline in the presence of Cs
2
CO
3
. This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8
H
-isoquinolino[1,2-
b
]quinazolin-8-ones in good yields.
Graphical abstract</description><subject>Analytical Chemistry</subject><subject>Carbonyls</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Dehydration</subject><subject>Diketones</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Proline</subject><subject>Theoretical and Computational Chemistry</subject><issn>0026-9247</issn><issn>1434-4475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9UU1vFSEUJUYTn7V_wBWJ294WGD6GZfOitkkTN-3KNIQBxkczhQrzjNPf4o-V6Zi4cwHce-45h9wchD5Qck4JURe1XUQCoRoI4x0B-QrtKO84cK7Ea7QjhEnQjKu36F2tD6T1nHQ79Psy4TCO0cWQZlyXNB9CjRXnEUs4LL7kXwtIeAzzYZlAnEnw8QWG_gpizT-OMeWpnW_0jMFwv_b2eUWgh5xCxT-jxRbvj9fg7Gyn5Tl47IN1y2TnmBO2yeOUG7TablBp47V4j96Mdqrh9O97gu4-f7rdX8HN1y_X-8sbcJ2QM1AnNLd2EF4HpvyggyMqUOc965kOdAj9IK0WdOyVprYTPRmZcLrnigjLZHeCPm6-T6UtFOpsHvKxpPalYUwQyVSvVhbbWK7kWksYzVOJj7YshhKzpmC2FExLwbykYFZRt4lqI6fvofyz_o_qD4jGi9I</recordid><startdate>20190701</startdate><enddate>20190701</enddate><creator>Miao, Wei-Qing</creator><creator>Liu, Jian-Quan</creator><creator>Wang, Xiang-Shan</creator><general>Springer Vienna</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-0077-7819</orcidid></search><sort><creationdate>20190701</creationdate><title>An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction</title><author>Miao, Wei-Qing ; Liu, Jian-Quan ; Wang, Xiang-Shan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-1c594aab5d9e27db9ec07e1cdd2829e1be8b6a951f8791a3580f25c984705a263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Analytical Chemistry</topic><topic>Carbonyls</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Dehydration</topic><topic>Diketones</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Proline</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miao, Wei-Qing</creatorcontrib><creatorcontrib>Liu, Jian-Quan</creatorcontrib><creatorcontrib>Wang, Xiang-Shan</creatorcontrib><collection>CrossRef</collection><jtitle>Monatshefte für Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miao, Wei-Qing</au><au>Liu, Jian-Quan</au><au>Wang, Xiang-Shan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction</atitle><jtitle>Monatshefte für Chemie</jtitle><stitle>Monatsh Chem</stitle><date>2019-07-01</date><risdate>2019</risdate><volume>150</volume><issue>7</issue><spage>1305</spage><epage>1315</epage><pages>1305-1315</pages><issn>0026-9247</issn><eissn>1434-4475</eissn><abstract>A novel and efficient annulation of pentane-2,4-dione with 2-(2-bromophenyl)quinazolin-4(3
H
)-one was disclosed in DMF catalyzed by CuI/
l
-proline in the presence of Cs
2
CO
3
. This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8
H
-isoquinolino[1,2-
b
]quinazolin-8-ones in good yields.
Graphical abstract</abstract><cop>Vienna</cop><pub>Springer Vienna</pub><doi>10.1007/s00706-019-02430-6</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-0077-7819</orcidid></addata></record> |
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| identifier | ISSN: 0026-9247 |
| ispartof | Monatshefte für Chemie, 2019-07, Vol.150 (7), p.1305-1315 |
| issn | 0026-9247 1434-4475 |
| language | eng |
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| source | Springer Link |
| subjects | Analytical Chemistry Carbonyls Chemical reactions Chemical synthesis Chemistry Chemistry and Materials Science Chemistry/Food Science Dehydration Diketones Inorganic Chemistry Organic Chemistry Original Paper Physical Chemistry Proline Theoretical and Computational Chemistry |
| title | An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction |
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