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Synthesis of Aryl-Substituted 3,3a,4,5-Tetrahydropyrrolo[1,2-a] quinolin-1(2H)-ones and 2,3,4,4a,5,6-Hexahydro-1H-pyrido[1,2-a]quinolin-1-ones
| Content Provider | Scilit |
|---|---|
| Author | Bunce, Richard A. Watts, Field M. |
| Copyright Year | 2018 |
| Description | A new route to the title benzo-fused angular tricyclic amides 3,3a,4,5-tetrahydropyrrolo- and 2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinolin-1-ones is reported from 1-(tert-butyl) 6-ethyl 3-oxohexanedioate and 1-(tert-butyl) 7-ethyl 3-oxoheptanedioate. Alkylation of these β-keto diesters with a series of 2-nitrobenzyl bromides followed by acid hydrolysis and decarboxylation gives ethyl 6-(2-nitrophenyl)-4-oxohexanoates and ethyl 7-(2-nitrophenyl)-5-oxoheptanoates, respectively. Reductive amination under hydrogenation conditions followed by ester hydrolysis and condensative ring closure affords the final lactam products. The reactions proceed cleanly and only two chromatographic purifications are required. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1609940.pdf |
| Ending Page | 572 |
| Page Count | 9 |
| Starting Page | 564 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-0037-1609940 |
| Journal | Synthesis |
| Issue Number | 02 |
| Volume Number | 51 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2018-09-05 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Benzo-fused Lactams Alkylation–decarboxylation Reductive Amination |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
