34016-32-5Relevant academic research and scientific papers
Photochemistry of ortho -Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent Control
Chaabouni,Pinkerton,Abid,Galaup,Chassaing
, p. 2614 - 2618 (2017/10/06)
The light-promoted potential of ortho -azidocinnamoyl compounds is evaluated for heterocycle synthesis. Depending on the nature of the solvent, 2-acylated indoles were obtained under aprotic conditions, whereas the use of a protic medium led to 2-substituted quinolines. The synthetic significance of this metal-free method is that, by simply changing the solvent, the reaction outcome can be directed towards different key heterocyclic scaffolds.
First Transformations of Pyranoindol-3-ones to Salvadoricine and 2,3-Diacylindoles
Pindur, Ulf,Erfanian-Abdoust, H.
, p. 145 - 147 (2007/10/02)
The readily available methylated pyranoindol-3-ones 1a and 1 b 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.
