Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on th...
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.12.32 |
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doaj-0bd2ab57db274dc58709e4b545811f012021-02-02T01:03:03ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-02-0112130130810.3762/bjoc.12.321860-5397-12-32Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-dionesPing Qian0Bingnan Du1Wei Jiao2Haibo Mei3Jianlin Han4Yi Pan5School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, ChinaSchool of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, ChinaSchool of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, ChinaSchool of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, ChinaSchool of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, ChinaSchool of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, ChinaAn oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C–C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield.https://doi.org/10.3762/bjoc.12.32C(sp3)–H bond functionalizationcyclizationdihydroisoquinolin-1(2H)-oneN-allylbenzamidesoxidation |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Ping Qian Bingnan Du Wei Jiao Haibo Mei Jianlin Han Yi Pan |
| spellingShingle |
Ping Qian Bingnan Du Wei Jiao Haibo Mei Jianlin Han Yi Pan Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones Beilstein Journal of Organic Chemistry C(sp3)–H bond functionalization cyclization dihydroisoquinolin-1(2H)-one N-allylbenzamides oxidation |
| author_facet |
Ping Qian Bingnan Du Wei Jiao Haibo Mei Jianlin Han Yi Pan |
| author_sort |
Ping Qian |
| title |
Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones |
| title_short |
Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones |
| title_full |
Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones |
| title_fullStr |
Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones |
| title_full_unstemmed |
Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones |
| title_sort |
cascade alkylarylation of substituted n-allylbenzamides for the construction of dihydroisoquinolin-1(2h)-ones and isoquinoline-1,3(2h,4h)-diones |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2016-02-01 |
| description |
An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C–C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield. |
| topic |
C(sp3)–H bond functionalization cyclization dihydroisoquinolin-1(2H)-one N-allylbenzamides oxidation |
| url |
https://doi.org/10.3762/bjoc.12.32 |
| work_keys_str_mv |
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