Wani, Imtiyaz Ahmad; Bhattacharyya, Aditya; Sayyad, Masthanvali; Ghorai, Manas K. published an article in 2018, the title of the article was Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles.Application In Synthesis of 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:
Direct and expedient access to densely substituted tetrahydrocarbazoles I [R1 = H, F; R2 = H, Me, CH2CH:CH2; R3 = OMe, OEt, Ph] and tetrahydrocycloheptadiindoles bearing multiple contiguous stereocenteres II [R1 = H, F, Cl, Me] were achieved via a two-fold divergent diastereoselective (dr up to >99:1) transformation of 2-vinylindoles. The high-yielding conversions (yield up to 87%) that were amenable for a wide range of substituted 2-vinylindoles proceeded through Lewis acid-catalyzed [4 + 2] and [4 + 3] cyclization-aromatization cascade reactions, resp., involving a heretofore-unprecedented reversal of the polarity (umpolung) of 2-vinylindoles. The two synthetic routes were effortlessly transposable into each other by merely modulating the temperature to furnished the corresponding products in a selective and exclusive fashion. In addition, another novel synthetic route to tetrahydroindolocarbazoles was developed that advances via a formal [4+2] cyclization of 4-vinylindoles involving sequential C3 Michael addition-dearomatization-aromatization cascade reactions. Diastereo- and chemoselective preparation of tetrahydrocarbazoles and tetrahydrocycloheptadiindoles via Fe(OTf)3 catalyzed tandem cyclization-aromatization of vinylindoles. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Application In Synthesis of 1,5-Dimethyl-1H-indole-2-carbaldehyde
The Article related to tetrahydrocarbazole preparation diastereoselective chemoselective, tetrahydrocycloheptadiindole preparation diastereoselective chemoselective, vinylindole iron trifluoromethanesulfonate catalyst tandem cyclization aromatization and other aspects.Application In Synthesis of 1,5-Dimethyl-1H-indole-2-carbaldehyde
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles