6533b85bfe1ef96bd12bb38e
RESEARCH PRODUCT
ChemInform Abstract: First Transformations of Pyrano(3,4-b)indol-3-ones to Salvadoricine and 2,3-Diacylindoles.
Houshang Erfanian-abdoustUlf Pindursubject
Nitrosobenzenechemistry.chemical_compoundHydrolysischemistryYield (chemistry)Substrate (chemistry)General MedicineMolecular oxygenMedicinal chemistryCatalysisdescription
The readily available methylated pyrano[3,4-b]indol-3-ones 1a and 1b were hydrolyzed to furnish the 2-acetylindol-3-alkanoic acids 2 and 4. Compound 2 was easily transformed selectively to 2-acetyl-3-methylindole (3, salvadoricine). Substrate 1b reacts with molecular oxygen from the air only in the presence of a catalyst to give 2,3-diacetylindole (5) while 1a reacts with nitrosobenzene via a proposed Diels-Alder step to yield 2-acetylindole-3-carbaldehyde (6). The latter product can also be obtained in low yield from the reaction of 1a with molecular oxygen from the air.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-08-21 | ChemInform |