Reaction of Indole Carboxylic Acid/Amide with Propargyl Alcohols: [4+3]-Annulation, Unexpected 3-to 2-Carboxylate/Amide Migration, and Decarboxylative Cyclization
1-Methylindole-3-carboxamides react with substituted propargyl alcohols to afford lactams by [4 + 3]-annulation and carboxamide group migration to the indole-2-position. In contrast, indole-2-carboxylic acids/amides form fused seven membered lactones/lactams (oxepinoindolones/azepinoindolones) upon...
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| Vydáno v: | Organic letters Ročník 21; číslo 14; s. 5447 - 5451 |
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| Hlavní autoři: | , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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WASHINGTON
Amer Chemical Soc
19.07.2019
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| ISSN: | 1523-7060, 1523-7052 |
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| Abstract | 1-Methylindole-3-carboxamides react with substituted propargyl alcohols to afford lactams by [4 + 3]-annulation and carboxamide group migration to the indole-2-position. In contrast, indole-2-carboxylic acids/amides form fused seven membered lactones/lactams (oxepinoindolones/azepinoindolones) upon treatment with substituted propargyl alcohols using catalytic Cu(OTf)(2). Decarboxylative cyclization of 1-methylindole-2- or indole-3-carboxylic acids with substituted propargyl alcohols under Lewis (for 1-methylindole-2-carboxylic acid) or Bronsted (for 1-methylindole-3-carboxylic acid) acid catalysis gives the same 3,4-dihydrocyclopentaindoles, demonstrating 3- to 2-carboxylate migration in the latter case. |
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| AbstractList | 1-Methylindole-3-carboxamides react with substituted propargyl alcohols to afford lactams by [4 + 3]-annulation and carboxamide group migration to the indole-2-position. In contrast, indole-2-carboxylic acids/amides form fused seven membered lactones/lactams (oxepinoindolones/azepinoindolones) upon treatment with substituted propargyl alcohols using catalytic Cu(OTf)(2). Decarboxylative cyclization of 1-methylindole-2- or indole-3-carboxylic acids with substituted propargyl alcohols under Lewis (for 1-methylindole-2-carboxylic acid) or Bronsted (for 1-methylindole-3-carboxylic acid) acid catalysis gives the same 3,4-dihydrocyclopentaindoles, demonstrating 3- to 2-carboxylate migration in the latter case. 1-Methylindole-3-carboxamides react with substituted propargyl alcohols to afford lactams by [4 + 3]-annulation and carboxamide group migration to the indole-2-position. In contrast, indole-2-carboxylic acids/amides form fused seven-membered lactones/lactams (oxepinoindolones/azepinoindolones) upon treatment with substituted propargyl alcohols using catalytic Cu(OTf) . Decarboxylative cyclization of 1-methylindole-2- or indole-3-carboxylic acids with substituted propargyl alcohols under Lewis (for 1-methylindole-2-carboxylic acid) or Brønsted (for 1-methylindole-3-carboxylic acid) acid catalysis gives the same 3,4-dihydrocyclopentaindoles, demonstrating 3- to 2-carboxylate migration in the latter case. |
| Author | Swamy, K. C. Kumara Debnath, Shubham Selvaraj, Karuppu |
| Author_xml | – sequence: 1 givenname: Karuppu surname: Selvaraj fullname: Selvaraj, Karuppu organization: Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India – sequence: 2 givenname: Shubham surname: Debnath fullname: Debnath, Shubham organization: Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India – sequence: 3 givenname: K. C. Kumara orcidid: 0000-0002-7617-706X surname: Swamy fullname: Swamy, K. C. Kumara email: kckssc@uohyd.ac.in organization: Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31246037$$D View this record in MEDLINE/PubMed |
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| Keywords | 2-INDOLYLMETHANOLS CASCADE REACTIONS 3-INDOLYLMETHANOLS ANNULATION ACIDS TANDEM CYCLIZATION STEREOSELECTIVE-SYNTHESIS AZIDE CYCLOADDITION CHEMISTRY ASYMMETRIC TOTAL-SYNTHESIS ENANTIOSELECTIVE CONSTRUCTION |
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| Title | Reaction of Indole Carboxylic Acid/Amide with Propargyl Alcohols: [4+3]-Annulation, Unexpected 3-to 2-Carboxylate/Amide Migration, and Decarboxylative Cyclization |
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