Synthesis of Indolines via a SmI 2 Promoted Domino Nitro Reduction–Intramolecular aza ‐Michael Reaction
A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza ‐Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2‐(2‐nitrophenyl) acetaldehyde deriv...
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| Published in: | Journal of heterocyclic chemistry Vol. 52; no. 1; pp. 54 - 58 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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01-01-2015
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| Abstract | A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular
aza
‐Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2‐(2‐nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This “one pot” strategy also permitted the expeditious synthesis of a 1,2,3,4‐tetrahydroquinoline, whereas the seven‐membered 2,3,4,5‐tetrahydrobenzoazepines compounds were not formed under these reaction conditions. |
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| AbstractList | A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular
aza
‐Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2‐(2‐nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This “one pot” strategy also permitted the expeditious synthesis of a 1,2,3,4‐tetrahydroquinoline, whereas the seven‐membered 2,3,4,5‐tetrahydrobenzoazepines compounds were not formed under these reaction conditions. |
| Author | Taylor, Jason G. Nagem, Tanus J. Ferreira Ramos, Josierika A. Araújo, Carolina S. |
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| Cites_doi | 10.1021/jo100320j 10.1039/np9961300073 10.1038/ja.2010.169 10.1002/hlca.19840670520 10.1021/ol902061j 10.1039/p19730000696 10.1039/a800280k 10.1021/jo00160a026 10.1021/jo050655o 10.1080/00397911.2010.492080 10.1515/HC.2011.043 10.1021/ol102341n 10.1016/S0040-4020(99)00455-X 10.1002/ejoc.200900787 10.1021/jo991899 10.1248/cpb.56.1367 10.1016/S0040-4039(00)95413-3 10.1016/S0040-4039(00)61121-8 10.1021/jo052236x 10.1021/jo00177a010 10.1002/chem.201100649 10.1021/jo202467k 10.1002/ejoc.201000323 10.1021/ja305660a 10.1007/s10593-010-0540-z 10.1021/jo005666q 10.1021/jo060308u |
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aza
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| Title | Synthesis of Indolines via a SmI 2 Promoted Domino Nitro Reduction–Intramolecular aza ‐Michael Reaction |
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