106103-38-2Relevant academic research and scientific papers
A NEW SYNTHESIS OF 1,2-DISUBSTITUED CARBAZOLES. ELECTROPHILIC CYANATION WITH VIEHE'S REAGENT.
Bergman, J.,Pelcman, B.
, p. 1939 - 1942 (1986)
Reaction of 2-ethylindole and 2-benzylindole with methyl vinyl ketone gives 1,2-dimethylcarbazole and 2-methyl-1-phenylcarbazole respectively.On thermolysis of the salt 11, obtained from the reaction of 2-(2-methylpropenyl)indole (7a) with Viehe's salt (10), the corresponding nitrile 13 is formed.
A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes
Banerjee, Ankush,Maji, Modhu Sudan
supporting information, p. 11521 - 11527 (2019/08/16)
A Br?nsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.
Total Synthesis of Marine Alkaloid Hyellazole and its Derivatives
Chakraborty, Suchandra,Saha, Chandan
, p. 2013 - 2021 (2018/05/15)
The total synthesis of the naturally occurring marine alkaloids hyellazole and chlorohyellazole was attempted from the corresponding easily accessible 2-methyl-1-ketotetrahydrocarbazoles obtained through the Japp–Klingemann reaction, followed by Fischer indole cyclization and subsequent Grignard coupling with phenylmagnesium bromide. Grignard coupling with 2-methyl-1-ketotetrahydrocarbazole unfortunately led directly to 2-methyl-1-phenylcarbazole through dehydration followed by aromatization through aerial oxidation, but application of the same reaction conditions to 6-chloro-2-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one, with careful treatment, led to the isolation of 6-chloro-2-methyl-1-phenyl-4,9-dihydro-3H-carbazole. However, selenium dioxide oxidation of this dihydrochloro derivative led to the formation of 6-chloro-2-methyl-1-phenyl-9H-carbazole. A different route was then adopted: a suitably substituted aromatic amine was used to establish the substitution pattern of the required carbazole derivative with a bromo group at C-1, and the required phenyl group at the 1-postion was then attached through Suzuki–Miyaura cross-coupling to furnish hyellazole.
Synthesis of substituted carbazoles and β-carbolines by cyclization of diketoindole derivatives
Duval, Eric,Cuny, Gregory D.
, p. 5411 - 5413 (2007/10/03)
A new route to substituted β-carbolines and carbazoles is described. Diketoindole intermediates, prepared by Friedel-Crafts acylations of 3-substituted indoles, have been converted to 3-hydroxycarbazoles and β-carbolines in good yields, 51-96% and 82-97%, respectively. This method also allows for the formation of 4-substituted β-carbolines. The application of this methodology to the synthesis of the natural products hyellazole and 6-chlorohyellazole is also described.
