Diastereoselective synthesis of tetrasubstituted-octahydro-3,6-diazacarbazoles and tetrasubstituted-3,6-diazacarbazoles via double Pictet-Spengler reaction
| Title | Diastereoselective synthesis of tetrasubstituted-octahydro-3,6-diazacarbazoles and tetrasubstituted-3,6-diazacarbazoles via double Pictet-Spengler reaction |
| Publication Type | Journal Article |
| Year of Publication | 2011 |
| Authors | Shumaila, AMA, Puranik, VG, Kusurkar, RS |
| Journal | Tetrahedron Letters |
| Volume | 52 |
| Issue | 21 |
| Pagination | 2661-2663 |
| Date Published | MAY |
| ISSN | 0040-4039 |
| Keywords | 2, 5-Bis(2-phenyl-1-aminoethyl)pyrrole, 6-diazacarbazoles, Diasteroselective Pictet-Spengler reaction, Glacial acetic acid, Tetrasubstituted-3, Tetrasubstituted-octahydro-3 |
| Abstract | Pictet-Spengler condensation of 2,5-bis(2-phenyl-1-aminoethyl)pyrrole using glacial acetic acid afforded only one diastereomer of unreported tetrasubstituted-octahydro-3,6-diazacarbazoles. These were readily dehydrogenated to tetrasubstituted-3,6-diazacarbazoles. The stereoselectivity in the Pictet-Spengler reaction has been demonstrated using single crystal X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2011.03.060 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.683 |
Divison category:
Center for Material Characterization (CMC)