Synthesis of tetrahydro-5-azaindoles and 5-azaindoles using pictet-spengler reaction-appreciable difference in products using different acid catalysts
| Title | Synthesis of tetrahydro-5-azaindoles and 5-azaindoles using pictet-spengler reaction-appreciable difference in products using different acid catalysts |
| Publication Type | Journal Article |
| Year of Publication | 2011 |
| Authors | Shumaila, AMA, Puranik, VG, Kusurkar, RS |
| Journal | Tetrahedron |
| Volume | 67 |
| Issue | 5 |
| Pagination | 936-942 |
| Date Published | FEB |
| ISSN | 0040-4020 |
| Keywords | 2-(Aryl)-2-(1H-pyrrol-2-yl)ethanamines, 4, 7-Disubstituted-5-azaindoles, 7-Disubstituted-tetrahydro-5-azaindoles, Diastereoselective Pictet-Spengler reaction |
| Abstract | Pictet-Spengler condensation of 2-(aryl)-2-(1H-pyrrol-2-yl)ethanamines using conventional acid catalysts like TMSCl or TFA resulted in the formation of substituted 5-azaindoles involving a tandem one pot four steps reaction sequence. By contrast use of glacial acetic acid furnished the targeted tetrahydro-5-azaindoles in diastereoselective manner. These were readily dehydrogenated to 5-azaindoles. (C) 2010 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2010.12.003 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.025 |
Divison category:
Center for Material Characterization (CMC)