Synthesis of carbazoles via an intramolecular cyclization of 2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines and their related molecules
Lee, CY; Lin, CF; Lee, JL; Chiu, CC; Lu, WD; Wu, MJ
| HERO ID | 658170 |
|---|---|
| In Press | No |
| Year | 2004 |
| Title | Synthesis of carbazoles via an intramolecular cyclization of 2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines and their related molecules |
| Authors | Lee, CY; Lin, CF; Lee, JL; Chiu, CC; Lu, WD; Wu, MJ |
| Journal | Journal of Organic Chemistry |
| Volume | 69 |
| Issue | 6 |
| Page Numbers | 2106-2110 |
| Abstract | Various 2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines 1a-g were treated with potassium tert-butoxide or potassium 3-ethylpentanoxide in NMP at 60 degrees C for 2 h to give the corresponding 5-substituted carbazoles 2a-g in 36-65% yields together with indoles 9a-g in 21-40% yields, respectively. Exposing the trifluoroacetamide analogues 10h-k under the same reaction conditions gave the carbazoles 2b-e in 37-57% yields and indoles 9b-e in 15-27% yields. Subsequent cyclizations of acetamide analogues 10a-g gave carbazoles 2a-g in 53-86% yields |
| Doi | 10.1021/jo0303158 |
| Pmid | 15058959 |
| Wosid | WOS:000220290900044 |
| Url | <Go to ISI>://WOS:000220290900044 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | 62-53-3; 75-36-5; Acetamides; Acetic Acids; Acids; Alkenes; Alkynes; analogs & derivatives; Aniline Compounds; Antineoplastic Agents; Butanols; Carbazoles; chemical synthesis; chemistry; Chlorides; Cyclization; Indoles; medical; PubMed 2000-07/21/04; Support,Non-U.S.Gov't; Trifluoroacetic Acid |
| Is Qa | No |