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...

Celý popis

Uložené v:
Podrobná bibliografia
Vydané v:Organic letters Ročník 21; číslo 14; s. 5447 - 5451
Hlavní autori: Selvaraj, Karuppu, Debnath, Shubham, Swamy, K. C. Kumara
Médium: Journal Article
Jazyk:English
Vydavateľské údaje: WASHINGTON Amer Chemical Soc 19.07.2019
Predmet:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2-INDOLYLMETHANOLS
CASCADE REACTIONS
3-INDOLYLMETHANOLS
ANNULATION
ACIDS
TANDEM CYCLIZATION
STEREOSELECTIVE-SYNTHESIS
AZIDE CYCLOADDITION CHEMISTRY
ASYMMETRIC TOTAL-SYNTHESIS
ENANTIOSELECTIVE CONSTRUCTION
ISSN:1523-7060, 1523-7052
On-line prístup:Zistit podrobnosti o prístupe
Tagy: Pridať tag
Žiadne tagy, Buďte prvý, kto otaguje tento záznam!
Popis
Shrnutí: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01686