The Cycloaddition Reaction of 3-Alkylindoles with p-Benzoquinone

Síntese e reatividade de azaindóis: aplicações na preparação de moléculas de interesse biológico

“…A ciclização de Reissert é um dos processos mais usados para a obtenção de 6-azaindóis [15][16][17][18] . Um método modificado [19][20][21][22][23] consiste na condensação de 9 com o dimetilformamida dimetilacetal, seguida de hidrogenação da nitroenamina obtida (Esquema 5).…”

Lewis Acid Catalyzed [3+2] Coupling of Indoles with Quinone Monoacetals or Quinone Imine Ketal

“…Soon after, Vincent4n and co‐workers reported FeCl 3 ‐mediated Friedel–Crafts hydroarylation with electrophilic N ‐acetylindoles and phenols to afford 3,3‐disubstituted indolines, followed by oxidation to yield the desired benzofuroindolines (Scheme , b). Furthermore, the direct construction of benzofuroindolines through the [3+2] coupling of 3‐substituted indoles with quinones was also documented by several groups 4o–4w. For example, in 2011, Chen and co‐workers employed a Brønsted acid catalyzed direct [3+2] coupling of β‐carbolines with quinones as a key strategy in the formal synthesis of (+)‐haplophytine (Scheme , c) 4w…”

Manufacturing synthesis of 5-hydroxy-2-methyl-1H-indole

“…There are a number of methods for the synthesis of indoles, such as the well known Fischer indole synthesis [10], Bartoli indole synthesis [11], LeimgruberBatcho indole synthesis [12], Reissert indole synthesis [13], Larock indole synthesis [14], Gassman indole synthesis [15], Bischler-Molau indole synthesis [16], and Nenitzescu indole synthesis [17][18][19]. More recently, many new methods of synthesizing various indoles have been published: (a) palladium (II) catalyzed ring closure [20][21][22][23][24][25][26][27], (b) copper (I/II) catalyzed cyclization [28][29][30], and (c) other indole formation [31][32][33][34][35][36][37].…”