Advancing the Morita-Baylis-Hillman chemistry of 1-formyl--carbolines for the synthesis of indolizinoindole derivatives
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Singh, Virender
Hutait, Samiran Batra, Sanjay |
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| Date |
2010-08-23T10:32:13Z
2010-08-23T10:32:13Z 2010 |
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| Identifier |
Eur. J. Org. Chem. 2010, 3684–3691
http://hdl.handle.net/123456789/572 |
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| Description |
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.
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240947 bytes
application/pdf |
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| Language |
en
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| Relation |
CDRI Communication no. 7935
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| Subject |
Morita-Baylis-Hillman
beta-carboline indolizinoindole PBr3 Harmicine Homofascaplysin |
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| Title |
Advancing the Morita-Baylis-Hillman chemistry of 1-formyl--carbolines for the synthesis of indolizinoindole derivatives
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| Type |
Article
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