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| Title: | Advancing the Morita-Baylis-Hillman chemistry of 1-formyl--carbolines for the synthesis of indolizinoindole derivatives |
| Authors: | Singh, Virender
Hutait, Samiran
Batra, Sanjay |
| Keywords: | Morita-Baylis-Hillman
beta-carboline
indolizinoindole
PBr3
Harmicine
Homofascaplysin |
| Issue Date: | 2010 |
| Citation: | Eur. J. Org. Chem. 2010, 3684–3691 |
| Series/Report no.: | CDRI Communication no. 7935 |
| Abstract: | The chemistry of the Morita-Baylis-Hillman adducts of 1-formyl-beta-carbolines has been extended for obtaining indolizinoindole derivatives which mimic the harmicine and homofascaplysin frameworks. Adduct of N-substituted methyl 1-formyl-9H-beta-carboline-3-carboxylate upon bromination followed by aqueous work up results in formation of indolizinoindole derivative. On the other hand N-substituted 1-formyl-9H-beta¢-carboline yielded similar product in one-pot via DABCO-promoted reaction of activated alkene. Alternatively the DMAP-mediated Morita-Baylis-Hillman reaction of N-substituted methyl 1-formyl-9H-beta-carboline-3-carboxylate with cycloalkenones yielded adducts, which cyclizes intramolecularly in the presence of PBr3 to yield compounds with homofascaplysin framework. In contrast DMAP-mediated reaction of N-substituted 1-formyl-beta-carboline with cyclohexenone directly gave product with similar framework in a single step. |
| URI: | http://hdl.handle.net/123456789/572 |
| Appears in Collections: | Medicinal and Process Chemistry
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| S.BATRA.pdf | | 235Kb | Adobe PDF | View/Open |
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