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| Title: | Synthesis of substituted 1H- and 3H-1-benzazepines: Rearrangement of 2-alkoxycarbonyl-1H-1-benzazepines to isoquinolines |
| Authors: | Singh, Vijay
Batra, Sanjay |
| Keywords: | Baylis-Hillman reaction
SnCl2.2H2O
Nitrogen heterocycles
Rearrangement. |
| Issue Date: | 2007 |
| Citation: | Eur. J. Org. Chem., 2970-2979 ( 2007) |
| Series/Report no.: | CDRI Communication no. 7149 |
| Abstract: | The SnCl2-mediated reduction of nitro groups in 2-nitro-4-(2-nitro-benzylidene)-alkanoates and 4-nitro-2-(2-nitro-alkylidene)-alkanoates afforded via SN2′ reaction of ethyl nitroacetate and nitroethane with the acetyl derivatives of Baylis-Hillman adducts afforded by 2-nitro-substituted benzaldehydes leads to facile synthesis of substituted 1H-1-benzazepine and 3H-1-benzazepine. During the study an unprecedented rearrangement of 2-alkoxycarbonyl-1H-benzazepine to substituted isoquinoline has been observed. |
| URI: | http://hdl.handle.net/123456789/39 |
| Appears in Collections: | Medicinal and Process Chemistry
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| sbatra-7149-EurJOC-2007.pdf | | 178Kb | Adobe PDF | View/Open |
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