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| Field | Value |
| Title | Design and synthesis of 1-Benzazepine derivatives by strategic utilization of Suzuki-Miyaura cross-coupling, Aza-Claisen rearrangement and ring-closing metathesis |
| Names |
KOTHA, S
SHAH, VR |
| Date Issued | 2008 (iso8601) |
| Abstract | A new and simple methodology has been realized for the synthesis of 7-substituted 2,3,4,5-tetrahydro-1-benzazepine derivatives with Suzuki-Miyaura cross-coupling, aza-Claisen rearrangement and ring-closing metathesis (RCM) the key steps. Here, o-allylacetanilide derivatives were obtained by Suzuki-Miyaura cross-couphng of the corresponding o-iodoacetanilides. The o-allylacetanilides, on N-allylation under phase-transfter catalysis conditions, provided diallyl derivatives as suitable precursors for RCM. These diallyl derivatives, on treatment with Grubbs' second-generation catalyst, gave the 1-benzazepine derivatives in moderate-to-good yields. These RCM products were found to be unstable and so they were hydrogenated to provide stable tetahydro-1-benzazepine derivatives 25-28. 1H-1-Benzazepin-2-one derivatives 44 and 45 were synthesized following a similar sequence. In addition, the aza-Claisen rearrangement was utilized as a key step in the preparation of RCM precursor 17. |
| Genre | Article; Proceedings Paper |
| Topic | Amino-Acid Derivatives |
| Identifier | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,(6)1054-1064 |