Synthesis of 4-carboxy-2,3-dihydrofuro(2,3-b)quinoline
✍ Scribed by P. Lakshminarayana; P. Shanmugam; K.K. Balasubramanian
- Publisher
- Elsevier Science
- Year
- 1970
- Tongue
- French
- Weight
- 97 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
It has been observed' that J-(l'-propenyl)P-quinolonee readily yield 2-methyl-2,3-dihydrofuro(2,3-b)quinolines on treatment with polyphosphorio acid whereas 3-vinyl-2-quinolones do not afford the oorreeponding dihydrofuroquinolines under the same conditions2. In this communication, we report a novel synthesis of 4_carboxy-2,3dihydrofuro(2,3-b)quinoline (V), utilising the hitherto unknown 4-oarboq-3vinyl-2-quinolone (II) l-l r II-~_
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The previous paper0 l-3 from thio laboratory describe the synthesis of 213 dihydrofuro(2,3-b)quinolines , and in no cane oould the dihydro compound be dehydrogeaated to the furoquinoline. The poaeibility that 3-vinyl-2-quinolones might oerve aa nece#aary precursor6 for the syntheaie of furo(2,3-b)qu
## Abstract Treatment of 2‐hydroxy‐, 2‐mercapto‐, and 2‐ethoxycarbonylamino‐benzonitriles **12** with 2‐fluoro‐ or 2‐nitrophenacylbromides **13** under alkaline conditions provided the corresponding benzofuran, benzothiophene, and indole intermediates **10**, respectivelly. Nucleophilic cyclization
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